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Total Synthesis of (±)-Lysergic Acid, Lysergol, and Isolysergol by Palladium-Catalyzed Domino Cyclization of Amino Allenes Bearing a Bromoindolyl Group

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Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan
Cite this: Org. Lett. 2008, 10, 22, 5239–5242
Publication Date (Web):October 28, 2008
https://doi.org/10.1021/ol8022648
Copyright © 2008 American Chemical Society

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    Abstract

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    Ergot alkaloids and their synthetic analogs have been reported to exhibit broad biological activity. We investigated direct construction of the C/D ring system of ergot alkaloids based on palladium-catalyzed domino cyclization of amino allenes. With this biscyclization as the key step, total synthesis of (±)-lysergic acid, (±)-lysergol, and (±)-isolysergol was achieved.

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    2. Brian J. Knight, Ryan C. Harbit, Joel M. Smith. Six-Step Synthesis of (±)-Lysergic Acid. The Journal of Organic Chemistry 2023, 88 (4) , 2158-2165. https://doi.org/10.1021/acs.joc.2c02564
    3. Nikhil R. Tasker, Peter Wipf. A Short Synthesis of Ergot Alkaloids and Evaluation of the 5-HT1/2 Receptor Selectivity of Lysergols and Isolysergols. Organic Letters 2022, 24 (40) , 7255-7259. https://doi.org/10.1021/acs.orglett.2c02569
    4. Yuhua Ge, Hang Wang, Hua-Nan Wang, Shu-Sheng Yu, Rui Yang, Xingyue Chen, Qin Zhao, Gang Chen. Biomimetic Total Syntheses of Ergot Alkaloids via Decarboxylative Giese Coupling. Organic Letters 2021, 23 (2) , 370-375. https://doi.org/10.1021/acs.orglett.0c03867
    5. Saikat Chaudhuri, Subhajit Bhunia, Avishek Roy, Mrinal K. Das, and Alakesh Bisai . Biomimetic Total Syntheses of Clavine Alkaloids. Organic Letters 2018, 20 (1) , 288-291. https://doi.org/10.1021/acs.orglett.7b03683
    6. Jianbo Lv, Bin Wang, Kuo Yuan, Yuan Wang, and Yanxing Jia . Regioselective Direct C-4 Functionalization of Indole: Total Syntheses of (−)-Agroclavine and (−)-Elymoclavine. Organic Letters 2017, 19 (13) , 3664-3667. https://doi.org/10.1021/acs.orglett.7b01681
    7. Haichao Liu, Xiwu Zhang, Dong Shan, Mallesham Pitchakuntla, Yongfan Ma, and Yanxing Jia . Total Syntheses of Festuclavine, Pyroclavine, Costaclavine, epi-Costaclavine, Pibocin A, 9-Deacetoxyfumigaclavine C, Fumigaclavine G, and Dihydrosetoclavine. Organic Letters 2017, 19 (12) , 3323-3326. https://doi.org/10.1021/acs.orglett.7b01504
    8. Karu Ramesh and Gedu Satyanarayana . A Domino Palladium-Catalyzed Cyclization: One-Pot Synthesis of 4b-Alkyl-10-phenyl-4b,5-dihydroindeno[2,1-a]indenes via Carbopalladation Followed by C–H Activation. The Journal of Organic Chemistry 2017, 82 (8) , 4254-4264. https://doi.org/10.1021/acs.joc.7b00254
    9. Bastian Milde, Martin Pawliczek, Peter G. Jones, and Daniel B. Werz . Enantioselective Total Synthesis of (+)-Lysergol: A Formal anti-Carbopalladation/Heck Cascade as the Key Step. Organic Letters 2017, 19 (7) , 1914-1917. https://doi.org/10.1021/acs.orglett.7b00675
    10. Yandong Lu, Haosen Yuan, Shijie Zhou, and Tuoping Luo . Total Syntheses of (−)-Hibiscone C and Lysergine: A Cyclization/Fragmentation Strategy. Organic Letters 2017, 19 (3) , 620-623. https://doi.org/10.1021/acs.orglett.6b03778
    11. Haosen Yuan, Zhixian Guo, and Tuoping Luo . Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity. Organic Letters 2017, 19 (3) , 624-627. https://doi.org/10.1021/acs.orglett.6b03779
    12. Shun-ichi Nakano, Naoya Inoue, Yasumasa Hamada, and Tetsuhiro Nemoto . Pd-Catalyzed Cascade Cyclization by Intramolecular Heck Insertion of an Allene–Allylic Amination Sequence: Application to the Synthesis of 3,4-Fused Tricyclic Indoles. Organic Letters 2015, 17 (11) , 2622-2625. https://doi.org/10.1021/acs.orglett.5b00973
    13. Hiroaki Ohno . Synthesis and Applications of Vinylaziridines and Ethynylaziridines. Chemical Reviews 2014, 114 (16) , 7784-7814. https://doi.org/10.1021/cr400543u
    14. Qiang Liu, Yu-An Zhang, Ping Xu, and Yanxing Jia . Total Synthesis of (+)-Lysergic Acid. The Journal of Organic Chemistry 2013, 78 (21) , 10885-10893. https://doi.org/10.1021/jo4018777
    15. Satoshi Umezaki, Satoshi Yokoshima, and Tohru Fukuyama . Total Synthesis of Lysergic Acid. Organic Letters 2013, 15 (16) , 4230-4233. https://doi.org/10.1021/ol4019562
    16. Bingxin Liu, Xiaohu Hong, Dong Yan, Shuguang Xu, Xiaomei Huang, and Bin Xu . Palladium-Catalyzed Tandem Allenyl and Aryl C–N Bond Formation: Efficient Access to N-Functionalized Multisubstituted Indoles. Organic Letters 2012, 14 (17) , 4398-4401. https://doi.org/10.1021/ol3018775
    17. Somasundharam Periyaraja, Asit Baran Mandal, and Ponnusamy Shanmugam . Unprecedented Binary Cu(I)/Cu(II) Catalyzed One-Pot, Three-Component Synthesis and Evaluation of Luminescent Property of 2-Amino-3-iminoethenylidene-2-indolones: A New Class of Merocyanine Dye Analogues. Organic Letters 2011, 13 (19) , 4980-4983. https://doi.org/10.1021/ol2022164
    18. Qiang Liu and Yanxing Jia . Total Synthesis of (+)-Lysergic Acid. Organic Letters 2011, 13 (18) , 4810-4813. https://doi.org/10.1021/ol2018467
    19. Akira Iwata, Shinsuke Inuki, Shinya Oishi, Nobutaka Fujii, and Hiroaki Ohno . Formal Total Synthesis of (+)-Lysergic Acid via Zinc(II)-Mediated Regioselective Ring-Opening Reduction of 2-Alkynyl-3-indolyloxirane. The Journal of Organic Chemistry 2011, 76 (13) , 5506-5512. https://doi.org/10.1021/jo2008324
    20. Shinsuke Inuki, Akira Iwata, Shinya Oishi, Nobutaka Fujii, and Hiroaki Ohno . Enantioselective Total Synthesis of (+)-Lysergic Acid, (+)-Lysergol, and (+)-Isolysergol by Palladium-Catalyzed Domino Cyclization of Allenes Bearing Amino and Bromoindolyl Groups. The Journal of Organic Chemistry 2011, 76 (7) , 2072-2083. https://doi.org/10.1021/jo102388e
    21. Egle M. Beccalli, Alice Bernasconi, Elena Borsini, Gianluigi Broggini, Micol Rigamonti, and Gaetano Zecchi . Tunable Pd-Catalyzed Cyclization of Indole-2-carboxylic Acid Allenamides: Carboamination vs Microwave-Assisted Hydroamination. The Journal of Organic Chemistry 2010, 75 (20) , 6923-6932. https://doi.org/10.1021/jo101501u
    22. Shinsuke Inuki, Yuji Yoshimitsu, Shinya Oishi, Nobutaka Fujii and Hiroaki Ohno. Ring-Construction/Stereoselective Functionalization Cascade: Total Synthesis of Pachastrissamine (Jaspine B) through Palladium-Catalyzed Bis-cyclization of Propargyl Chlorides and Carbonates. The Journal of Organic Chemistry 2010, 75 (11) , 3831-3842. https://doi.org/10.1021/jo100544v
    23. Jason A. Deck and Stephen F. Martin. Enantioselective Synthesis of (+)-Isolysergol via Ring-Closing Metathesis. Organic Letters 2010, 12 (11) , 2610-2613. https://doi.org/10.1021/ol100819f
    24. Yusuke Ohta, Hiroaki Chiba, Shinya Oishi, Nobutaka Fujii and Hiroaki Ohno. Construction of Nitrogen Heterocycles Bearing an Aminomethyl Group by Copper-Catalyzed Domino Three-Component Coupling−Cyclization. The Journal of Organic Chemistry 2009, 74 (18) , 7052-7058. https://doi.org/10.1021/jo901328q
    25. Egle M. Beccalli, Gianluigi Broggini, Francesca Clerici, Simona Galli, Claire Kammerer, Micol Rigamonti and Silvia Sottocornola. Palladium-Catalyzed Domino Carbopalladation/5-exo-Allylic Amination of α-Amino Allenamides: An Efficient Entry to Enantiopure Imidazolidinones. Organic Letters 2009, 11 (7) , 1563-1566. https://doi.org/10.1021/ol900171g
    26. Soumya Kumar Sinha, Pintu Ghosh, Shubhanshu Jain, Siddhartha Maiti, Shaeel A. Al-Thabati, Abdulmohsen Ali Alshehri, Mohamed Mokhtar, Debabrata Maiti. Transition-metal catalyzed C–H activation as a means of synthesizing complex natural products. Chemical Society Reviews 2023, 52 (21) , 7461-7503. https://doi.org/10.1039/D3CS00282A
    27. Xue‐Song Zhang, Ya‐Ping Han, Yuecheng Zhang, Yong‐Min Liang. Transition‐Metal‐Catalyzed Transformations Involving the Heck Reaction. Advanced Synthesis & Catalysis 2023, 365 (15) , 2436-2466. https://doi.org/10.1002/adsc.202300476
    28. Raghavendra Ramachanderan, Stefan Schramm, Bernd Schaefer. Migraine drugs. ChemTexts 2023, 9 (2) https://doi.org/10.1007/s40828-023-00178-5
    29. Michael J. Nutt, Nick Woolf, Scott G. Stewart, . Overview of the synthetic approaches to lysergic acid as a precursor to the psychedelic LSD. Australian Journal of Chemistry 2023, 76 (5) , 279-287. https://doi.org/10.1071/CH23055
    30. Michał K. Jastrzębski, Agnieszka A. Kaczor, Tomasz M. Wróbel. Methods of Lysergic Acid Synthesis—The Key Ergot Alkaloid. Molecules 2022, 27 (21) , 7322. https://doi.org/10.3390/molecules27217322
    31. Shaheera Tabassum, Ameer Fawad Zahoor, Sajjad Ahmad, Razia Noreen, Samreen Gul Khan, Hamad Ahmad. Cross-coupling reactions towards the synthesis of natural products. Molecular Diversity 2022, 26 (1) , 647-689. https://doi.org/10.1007/s11030-021-10195-6
    32. K. R. Holman, A. M. Stanko, S. E. Reisman. Palladium-catalyzed cascade cyclizations involving C–C and C–X bond formation: strategic applications in natural product synthesis. Chemical Society Reviews 2021, 50 (14) , 7891-7908. https://doi.org/10.1039/D0CS01385D
    33. Hiroaki Ohno, Shinsuke Inuki. Nonbiomimetic total synthesis of indole alkaloids using alkyne-based strategies. Organic & Biomolecular Chemistry 2021, 19 (16) , 3551-3568. https://doi.org/10.1039/D0OB02577A
    34. Milos D. Jovanovic, Milos R. Petkovic, Vladimir M. Savic. Polycyclic Compounds from Allenes via Palladium-Mediated Intramolecular Carbopalladation/Nucleophilic Substitution Cascade Processes. Synthesis 2021, 53 (06) , 1035-1045. https://doi.org/10.1055/s-0040-1705994
    35. Nikhil R. Tasker, Peter Wipf. Biosynthesis, total synthesis, and biological profiles of Ergot alkaloids. 2021, 1-112. https://doi.org/10.1016/bs.alkal.2020.08.001
    36. Arpita Banerjee, Gautam Panda. Total synthesis of selected bioactive alkaloids, their structure–function relationships and molecular target interactions: A comparative synthetic analysis of tryptophan originated chiral pool approaches vs other synthons. Results in Chemistry 2021, 3 , 100215. https://doi.org/10.1016/j.rechem.2021.100215
    37. Haruka Takeuchi, Shinsuke Inuki, Kohei Nakagawa, Takaaki Kawabe, Atsuhiko Ichimura, Shinya Oishi, Hiroaki Ohno. Total Synthesis of Zephycarinatines via Photocatalytic Reductive Radical ipso ‐Cyclization. Angewandte Chemie International Edition 2020, 59 (47) , 21210-21215. https://doi.org/10.1002/anie.202009399
    38. Haruka Takeuchi, Shinsuke Inuki, Kohei Nakagawa, Takaaki Kawabe, Atsuhiko Ichimura, Shinya Oishi, Hiroaki Ohno. Total Synthesis of Zephycarinatines via Photocatalytic Reductive Radical ipso ‐Cyclization. Angewandte Chemie 2020, 132 (47) , 21396-21401. https://doi.org/10.1002/ange.202009399
    39. Shinsuke Inuki. Elucidation of Biological Mechanisms Using Synthetic Natural Products and Their Derivatives. YAKUGAKU ZASSHI 2020, 140 (4) , 455-470. https://doi.org/10.1248/yakushi.19-00206
    40. Robert Connon, Patrick J. Guiry. A Tandem Asymmetric Friedel–Crafts Alkylation/Michael Addition: Synthesis of Novel Ergoline Derivatives. European Journal of Organic Chemistry 2019, 2019 (34) , 5950-5954. https://doi.org/10.1002/ejoc.201901007
    41. Tetsuhiro Nemoto. Synthesis of 3,4‐Fused Tricyclic Indoles Using 3‐Alkylidene Indolines as Versatile Precursors. The Chemical Record 2019, 19 (2-3) , 320-332. https://doi.org/10.1002/tcr.201800043
    42. Tetsuhiro Nemoto, Shingo Harada, Masaya Nakajima. Synthetic Methods for 3,4‐Fused Tricyclic Indoles via Indole Ring Formation. Asian Journal of Organic Chemistry 2018, 7 (9) , 1730-1742. https://doi.org/10.1002/ajoc.201800336
    43. Shun-ichi Nakano, Yasumasa Hamada, Tetsuhiro Nemoto. Enantioselective formal synthesis of (−)-aurantioclavine using Pd-catalyzed cascade cyclization and organocatalytic asymmetric aziridination. Tetrahedron Letters 2018, 59 (8) , 760-762. https://doi.org/10.1016/j.tetlet.2018.01.033
    44. Rentaro Kanno, Satoshi Yokoshima, Motomu Kanai, Tohru Fukuyama. Total synthesis of (+)-lysergic acid. The Journal of Antibiotics 2018, 71 (2) , 240-247. https://doi.org/10.1038/ja.2017.80
    45. Egle M. Beccalli, Gianluigi Broggini, Michael S. Christodoulou, Sabrina Giofrè. Transition Metal-Catalyzed Intramolecular Amination and Hydroamination Reactions of Allenes. 2018, 1-71. https://doi.org/10.1016/bs.adomc.2018.02.003
    46. Subhajit Bhunia, Saikat Chaudhuri, Subhadip De, K. Naresh Babu, Alakesh Bisai. An expeditious route to the synthesis of the enantioenriched tetracyclic core of ergot alkaloids via an organocatalytic aldol reaction. Organic & Biomolecular Chemistry 2018, 16 (14) , 2427-2437. https://doi.org/10.1039/C7OB03069J
    47. Christina Despotopoulou, Sean C. McKeon, Robert Connon, Vincent Coeffard, Helge Müller‐Bunz, Patrick J. Guiry. Application of a One‐Pot Friedel–Crafts Alkylation/Michael Addition Methodology to the Asymmetric Synthesis of Ergoline Derivatives. European Journal of Organic Chemistry 2017, 2017 (45) , 6734-6738. https://doi.org/10.1002/ejoc.201701480
    48. Subhajit Bhunia, Saikat Chaudhuri, Alakesh Bisai. Total Syntheses of Pyroclavine, Festuclavine, Lysergol, and Isolysergol via a Catalytic Asymmetric Nitro‐Michael Reaction. Chemistry – A European Journal 2017, 23 (47) , 11234-11238. https://doi.org/10.1002/chem.201702459
    49. Benxiang Zhang, Xiaoqing Wang, Chao Cheng, Deqian Sun, Chaozhong Li. Total Synthesis of (±)‐Corymine. Angewandte Chemie 2017, 129 (26) , 7592-7595. https://doi.org/10.1002/ange.201704086
    50. Benxiang Zhang, Xiaoqing Wang, Chao Cheng, Deqian Sun, Chaozhong Li. Total Synthesis of (±)‐Corymine. Angewandte Chemie International Edition 2017, 56 (26) , 7484-7487. https://doi.org/10.1002/anie.201704086
    51. Tse‐Lok Ho. Tetrakis(triphenylphosphine)palladium(0). 2017https://doi.org/10.1002/9780471264194.fos09648.pub6
    52. Tse‐Lok Ho, Mary Fieser, Rick Danheiser, William Roush, Janice Smith, Louis Fieser. Tetrakis(triphenylphosphine)palladium(0). 2017https://doi.org/10.1002/9780471264194.fos09648.pub7
    53. Haichao Liu, Yanxing Jia. Ergot alkaloids: synthetic approaches to lysergic acid and clavine alkaloids. Natural Product Reports 2017, 34 (4) , 411-432. https://doi.org/10.1039/C6NP00110F
    54. Yuta Suzuki, Yuito Tanaka, Shun‐ichi Nakano, Kosuke Dodo, Natsumi Yoda, Ken‐ichi Shinohara, Kazuko Kita, Atsushi Kaneda, Mikiko Sodeoka, Yasumasa Hamada, Tetsuhiro Nemoto. Platinum‐Catalyzed Friedel–Crafts‐Type C−H Coupling–Allylic Amination Cascade to Synthesize 3,4‐Fused Tricyclic Indoles. Chemistry – A European Journal 2016, 22 (13) , 4418-4421. https://doi.org/10.1002/chem.201600375
    55. Kiyoun Lee, Yam B. Poudel, Christopher M. Glinkerman, Dale L. Boger. Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs. Tetrahedron 2015, 71 (35) , 5897-5905. https://doi.org/10.1016/j.tet.2015.05.093
    56. Guilhem Henrion, Fabien Gagosz. Gold‐Promoted Sigmatropic Rearrangements. 2014, 1-86. https://doi.org/10.1002/9780470682531.pat0810
    57. David Tejedor, Sergio J. Álvarez‐Méndez, Juan M. López‐Soria, Víctor S. Martín, Fernando García‐Tellado. A Robust and General Protocol for the Lewis‐Base‐Catalysed Reaction of Alcohols and Alkyl Propiolates. European Journal of Organic Chemistry 2014, 2014 (1) , 198-205. https://doi.org/10.1002/ejoc.201301303
    58. Peng‐Fei Xu, Hao Wei. USE OF TRANSITION METAL–CATALYZED CASCADE REACTIONS IN NATURAL PRODUCT SYNTHESIS AND DRUG DISCOVERY. 2013, 283-331. https://doi.org/10.1002/9781118356654.ch7
    59. Tilman Lechel, Fabian Pfrengle, Hans‐Ulrich Reissig, Reinhold Zimmer. Three Carbons for Complexity! Recent Developments of Palladium‐Catalyzed Reactions of Allenes. ChemCatChem 2013, 5 (8) , 2100-2130. https://doi.org/10.1002/cctc.201200875
    60. Mehak Rohilla, Neetu Goel, Tej Vir Singh, P. Venugopalan, N. V. Suresh Kumar, K. Tewari. Theoretical and experimental studies on solubility and reactivity behavior of lysergol, elymoclavine, and dihydrolysergol. International Journal of Quantum Chemistry 2013, 113 (10) , 1427-1435. https://doi.org/10.1002/qua.24335
    61. Tse‐Lok Ho, Mary Fieser, Rick Danheiser, William Roush, Janice Smith, Louis Fieser. Tetrakis(triphenylphosphine)palladium(0). 2013, 463-467. https://doi.org/10.1002/9780471264194.fos09648.pub5
    62. Somasundharam Periyaraja, Ponnusamy Shanmugam, Asit Baran Mandal, Thiyagarajan Senthil Kumar, Perumal Ramamurthy. Unusual reactivity of 1-aminoanthraquinone in copper catalyzed multicomponent reaction with isatins and aryl alkynes: synthesis and photophysical properties of regioisomeric fluorescent 3-spiroheterocyclic 2-oxindoles. Tetrahedron 2013, 69 (14) , 2891-2899. https://doi.org/10.1016/j.tet.2013.02.037
    63. David Tejedor, Gabriela Méndez-Abt, Leandro Cotos, Fernando García-Tellado. Propargyl Claisen rearrangement: allene synthesis and beyond. Chem. Soc. Rev. 2013, 42 (2) , 458-471. https://doi.org/10.1039/C2CS35311C
    64. Stefan Bräse, Franziska Gläser, Carsten S. Kramer, Stephanie Lindner, Anna M. Linsenmeier, Kye-Simeon Masters, Anne C. Meister, Bettina M. Ruff, Sabilla Zhong. Ergot Alkaloids. 2013, 27-47. https://doi.org/10.1007/978-3-7091-1312-7_4
    65. Hiroaki Ohno. Recent Advances in the Construction of Polycyclic Compounds by Palladium‐Catalyzed Atom‐Economical Cascade Reactions. Asian Journal of Organic Chemistry 2013, 2 (1) , 18-28. https://doi.org/10.1002/ajoc.201200128
    66. Erik V. Van der Eycken, Jitender B. Bariwal, Jalpa J. Bariwal. Microwaves in the Synthesis of Natural Products. 2012, 843-896. https://doi.org/10.1002/9783527651313.ch19
    67. Hiroaki Ohno, Mutsumi Iuchi, Naoto Kojima, Takehiko Yoshimitsu, Nobutaka Fujii, Tetsuaki Tanaka. Double CH Functionalization in Sequential Order: Direct Synthesis of Polycyclic Compounds by a Palladium‐Catalyzed CH Alkenylation–Arylation Cascade. Chemistry – A European Journal 2012, 18 (17) , 5352-5360. https://doi.org/10.1002/chem.201103819
    68. Shichao Yu, Shengming Ma. Allenes in Catalytic Asymmetric Synthesis and Natural Product Syntheses. Angewandte Chemie International Edition 2012, 51 (13) , 3074-3112. https://doi.org/10.1002/anie.201101460
    69. Shichao Yu, Shengming Ma . Allene in katalytischer asymmetrischer Synthese und Naturstoffsynthese. Angewandte Chemie 2012, 124 (13) , 3128-3167. https://doi.org/10.1002/ange.201101460
    70. Koushik Goswami, Sibasish Paul, Sandesh T. Bugde, Surajit Sinha. Synthesis of optically active homotryptophan and its oxygen and sulfur analogues. Tetrahedron 2012, 68 (1) , 280-286. https://doi.org/10.1016/j.tet.2011.10.055
    71. Muriel Durandetti, Lucie Hardou, Rudy Lhermet, Mathieu Rouen, Jacques Maddaluno. Synthetic Applications of the Nickel‐Catalyzed Cyclization of Alkynes Combined with Addition Reactions in a Domino Process. Chemistry – A European Journal 2011, 17 (45) , 12773-12783. https://doi.org/10.1002/chem.201100967
    72. Chicco Manzuna Sapu, Jan‐E. Bäckvall, Jan Deska. Enantioselective Enzymatic Desymmetrization of Prochiral Allenic Diols. Angewandte Chemie International Edition 2011, 50 (41) , 9731-9734. https://doi.org/10.1002/anie.201103227
    73. Chicco Manzuna Sapu, Jan‐E. Bäckvall, Jan Deska. Enantioselektive enzymatische Desymmetrisierung prochiraler Allendiole. Angewandte Chemie 2011, 123 (41) , 9905-9908. https://doi.org/10.1002/ange.201103227
    74. Benito Alcaide, Pedro Almendros. Novel Cyclization Reactions of Aminoallenes. Advanced Synthesis & Catalysis 2011, 353 (14-15) , 2561-2576. https://doi.org/10.1002/adsc.201100160
    75. Tse‐Lok Ho, Mary Fieser, Rick Danheiser, William Roush, Janice Smith, Louis Fieser. Tetrakis(triphenylphosphine)palladium(0). 2011, 536-541. https://doi.org/10.1002/9780471264194.fos09648.pub4
    76. Jiajia Cheng, Xuefeng Jiang, Can Zhu, Shengming Ma. Palladium‐Catalyzed Three‐Component Tandem Cyclization Reaction of 2‐(2,3‐Allenyl)acylacetates, Organic Halides, and Amines: An Effective Protocol for the Synthesis of 4,5‐Dihydro‐1 H ‐pyrrole Derivatives. Advanced Synthesis & Catalysis 2011, 353 (10) , 1676-1682. https://doi.org/10.1002/adsc.201100002
    77. Egle M. Beccalli, Gianluigi Broggini, Andrea Fasana, Micol Rigamonti. Palladium-catalyzed C–N bond formation via direct C–H bond functionalization. Recent developments in heterocyclic synthesis. Journal of Organometallic Chemistry 2011, 696 (1) , 277-295. https://doi.org/10.1016/j.jorganchem.2010.09.078
    78. Yusuke Ohta. Introduction. 2011, 1-6. https://doi.org/10.1007/978-3-642-15473-7_1
    79. Annamaria Deagostino, Cristina Prandi, Silvia Tabasso, Paolo Venturello. The Heck Reaction Applied to 1,3- and 1,2-Unsaturated Derivatives, a Way towards Molecular Complexity. Molecules 2010, 15 (4) , 2667-2685. https://doi.org/10.3390/molecules15042667
    80. Minoru Ishikura, Koji Yamada, Takumi Abe. Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Natural Product Reports 2010, 27 (11) , 1630. https://doi.org/10.1039/c005345g
    81. Kimio Hirano, Yusuke Inaba, Toshiaki Watanabe, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno. . Advanced Synthesis & Catalysis 2010, 368. https://doi.org/10.1002/adsc.200900880
    82. Jonathon S. Russel, Erin T. Pelkey, Sarah J.P. Yoon-Miller. Chapter 5.2: Five-Membered Ring Systems: Pyrroles and Benzo Analogs. 2009, 145-178. https://doi.org/10.1016/S0959-6380(09)70033-9
    83. Darrin W. Hopper, Aimee L. Crombie, Jeremy J. Clemens, Soojin Kwon. Chapter 6.1: Six-Membered Ring Systems: Pyridine and Benzo Derivatives. 2009, 330-374. https://doi.org/10.1016/S0959-6380(09)70039-X
    84. Tohru Fukuyama, Tohru Inoue, Satoshi Yokoshima. Synthetic Studies toward (+)-Lysergic Acid: Construction of the Tetracyclic Ergoline Skeleton. HETEROCYCLES 2009, 79 (1) , 373. https://doi.org/10.3987/COM-08-S(D)42

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