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Total Synthesis of (±)-Trigonoliimine C via Oxidative Rearrangement of an Unsymmetrical Bis-Tryptamine

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    Total Synthesis of (±)-Trigonoliimine C via Oxidative Rearrangement of an Unsymmetrical Bis-Tryptamine
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    Department of Biochemistry, Division of Chemistry, The University of Texas Southwestern Medical Center at Dallas, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, United States
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    Cite this: J. Am. Chem. Soc. 2011, 133, 26, 10050–10053
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    https://doi.org/10.1021/ja203960b
    Published June 14, 2011
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    Abstract

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    We report the first total synthesis of (±)-trigonoliimine C, a member of a family of structurally complex alkaloids, in 10 steps from tryptamine and 6-methoxytryptamine. Our convergent synthetic strategy relies on a selective oxidative rearrangement of an unsymmetrical 2,2′-bis-tryptamine.

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    16. Takumi Abe and Koji Yamada . Dehydrative Mannich-Type Reaction for the Synthesis of Azepinobisindole Alkaloid Iheyamine A. Organic Letters 2018, 20 (5) , 1469-1472. https://doi.org/10.1021/acs.orglett.8b00330
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    49. Toshiki Yamashiro, Takumi Abe, Daisuke Sawada. Synthesis of 2-monosubstituted indolin-3-ones by cine -substitution of 3-azido-2-methoxyindolines. Organic Chemistry Frontiers 2022, 9 (7) , 1897-1903. https://doi.org/10.1039/D2QO00048B
    50. Fan Xu, Myles W. Smith. A general approach to 2,2-disubstituted indoxyls: total synthesis of brevianamide A and trigonoliimine C. Chemical Science 2021, 12 (41) , 13756-13763. https://doi.org/10.1039/D1SC03533A
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    54. Xi Yuan, Xudong Wu, Fei Peng, Haijun Yang, Changjin Zhu, Hua Fu. Organocatalytic asymmetric synthesis of arylindolyl indolin-3-ones with both axial and central chirality. Chemical Communications 2020, 56 (83) , 12648-12651. https://doi.org/10.1039/D0CC05432A
    55. Caroline Grundke, Nina Vierengel, Till Opatz. ‐Aminonitriles: From Sustainable Preparation to Applications in Natural Product Synthesis. The Chemical Record 2020, 20 (9) , 989-1016. https://doi.org/10.1002/tcr.202000066
    56. Vladimir P. Zaytsev, Dmitriy F. Mertsalov, Anastasiya M. Trunova, Anastasiya V. Khanova, Eugeniya V. Nikitina, Anna А. Sinelshchikova, Mikhail S. Grigoriev. Iodine Acetate as a Mild Selective Agent for the Wagner–Meerwein Rearrangement in 3a,6-Epoxyisoindoles. Chemistry of Heterocyclic Compounds 2020, 56 (7) , 930-935. https://doi.org/10.1007/s10593-020-02752-y
    57. Qing‐Xia Zhang, Yao Li, Jie Wang, Chen Yang, Cheng‐Jun Liu, Xin Li, Jin‐Pei Cheng. B(C 6 F 5 ) 3 /Chiral Phosphoric Acid Catalyzed Ketimine–Ene Reaction of 2‐Aryl‐3 H ‐indol‐3‐ones and α‐Methylstyrenes. Angewandte Chemie 2020, 132 (11) , 4580-4586. https://doi.org/10.1002/ange.201915226
    58. Qing‐Xia Zhang, Yao Li, Jie Wang, Chen Yang, Cheng‐Jun Liu, Xin Li, Jin‐Pei Cheng. B(C 6 F 5 ) 3 /Chiral Phosphoric Acid Catalyzed Ketimine–Ene Reaction of 2‐Aryl‐3 H ‐indol‐3‐ones and α‐Methylstyrenes. Angewandte Chemie International Edition 2020, 59 (11) , 4550-4556. https://doi.org/10.1002/anie.201915226
    59. Xue-Fei Jiang, Hao Tan, Hai-Lei Cui. FeCl 3 mediated dimerization of dihydropyrrolo[2,1- a ]isoquinolines and chlorination of tetrasubstituted pyrroles. Organic & Biomolecular Chemistry 2020, 18 (4) , 660-665. https://doi.org/10.1039/C9OB02607J
    60. Boora Ramesh, G. Ravi Kumar, Suresh Yarlagadda, B. Sridhar, B.V. Subba Reddy. BINOL-phosphoric acid catalyzed asymmetric Mannich addition of β-ketoesters to indolenines generated in situ by DDQ. Tetrahedron 2019, 75 (44) , 130620. https://doi.org/10.1016/j.tet.2019.130620
    61. Xigong Liu, Xue Yan, Yingde Tang, Cheng-Shi Jiang, Jin-Hai Yu, Kaiming Wang, Hua Zhang. Direct oxidative dearomatization of indoles: access to structurally diverse 2,2-disubstituted indolin-3-ones. Chemical Communications 2019, 55 (46) , 6535-6538. https://doi.org/10.1039/C9CC02956G
    62. Lalita Devi, Rashmi Shukla, Namrata Rastogi. Intramolecular trapping of ammonium ylides with N -benzoylbenzotriazoles in aqueous medium: direct access to the pseudoindoxyl scaffold. Organic & Biomolecular Chemistry 2019, 17 (1) , 135-139. https://doi.org/10.1039/C8OB02683A
    63. Takumi Abe, Koji Yamada, Syuhei Satake. Biomimetic Synthesis of Iheyamine A from Spirocyclic Oxindoles. HETEROCYCLES 2019, 99 (1) , 379. https://doi.org/10.3987/COM-18-S(F)30
    64. Ashley C. Lindsay, Se Hun Kim, Jonathan Sperry. Non-monoterpenoid azepinoindole alkaloids. Natural Product Reports 2018, 35 (12) , 1347-1382. https://doi.org/10.1039/C8NP00047F
    65. Cecilia Ciccolini, Michele Mari, Simone Lucarini, Fabio Mantellini, Giovanni Piersanti, Gianfranco Favi. Polycyclic Indolines by an Acid‐Mediated Intramolecular Dearomative Strategy: Reversing Indole Reactivity in the Pictet‐Spengler‐Type Reaction. Advanced Synthesis & Catalysis 2018, 360 (21) , 4060-4067. https://doi.org/10.1002/adsc.201800981
    66. Liwei Bu, Jiangtao Li, Yanli Yin, Baokun Qiao, Guobi Chai, Xiaowei Zhao, Zhiyong Jiang. Organocatalytic Asymmetric Cascade Aerobic Oxidation and Semipinacol Rearrangement Reaction: A Visible Light‐Induced Approach to Access Chiral 2,2‐Disubstituted Indolin‐3‐ones. Chemistry – An Asian Journal 2018, 13 (17) , 2382-2387. https://doi.org/10.1002/asia.201800446
    67. Rodney A. Fernandes. Latent Functionality. 2018, 229-257. https://doi.org/10.1002/9781119295266.ch9
    68. Suresh Yarlagadda, B. Sridhar, Basireddy Venkata Subba Reddy. Oxidative Asymmetric Aza‐Friedel–Crafts Alkylation of Indoles with 3‐Indolinone‐2‐carboxylates Catalyzed by a BINOL Phosphoric Acid and Promoted by DDQ. Chemistry – An Asian Journal 2018, 13 (10) , 1327-1334. https://doi.org/10.1002/asia.201800300
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    70. Nicholas M. Butler, Rudi Hendra, John B. Bremner, Anthony C. Willis, Leonardo Lucantoni, Vicky M. Avery, Paul A. Keller. Cascade reactions of indigo with oxiranes and aziridines: efficient access to dihydropyrazinodiindoles and spiro-oxazocinodiindoles. Organic & Biomolecular Chemistry 2018, 16 (33) , 6006-6016. https://doi.org/10.1039/C8OB00865E
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    73. Xurong Qin, Marcus Wen Yao Lee, Jianrong Steve Zhou. Nickel‐Catalyzed Asymmetric Reductive Heck Cyclization of Aryl Halides to Afford Indolines. Angewandte Chemie International Edition 2017, 56 (41) , 12723-12726. https://doi.org/10.1002/anie.201707134
    74. Eva Schendera, Stephanie Lerch, Thorsten von Drathen, Lisa‐Natascha Unkel, Malte Brasholz. Phosphoric Acid Catalyzed 1,2‐Rearrangements of 3‐Hydroxyindolenines to Indoxyls and 2‐Oxindoles: Reagent‐Controlled Regioselectivity Enabled by Dual Activation. European Journal of Organic Chemistry 2017, 2017 (22) , 3134-3138. https://doi.org/10.1002/ejoc.201700085
    75. O. L. Babii, A. A. Hodak, A. S. Peregudov, V. I. Polshakov, Z. A. Starikova, Yu. A. Borisov, Yu. V. Fedorov, V. S. Velezheva. Reinvestigation of dimerization of Z-N-alkylarylmethylideneindoxyls upon exposure to UV-vis radiation. Russian Chemical Bulletin 2017, 66 (2) , 350-354. https://doi.org/10.1007/s11172-017-1739-2
    76. Zilei Xia, Jiadong Hu, Yu-Qi Gao, Qizheng Yao, Weiqing Xie. Facile access to 2,2-disubstituted indolin-3-ones via a cascade Fischer indolization/Claisen rearrangement reaction. Chemical Communications 2017, 53 (54) , 7485-7488. https://doi.org/10.1039/C7CC03754F
    77. Sai-Shuai Wen, Zhao-Fang Zhou, Jun-An Xiao, Jun Li, Haoyue Xiang, Hua Yang. Facile oxidative cyclization to access C2-quaternary 2-hydroxy-indolin-3-ones: synthetic studies towards matemone. New Journal of Chemistry 2017, 41 (20) , 11503-11506. https://doi.org/10.1039/C7NJ02246H
    78. Ramandeep Kaur, Yuvraj Garg, Satyendra Kumar Pandey. A Short Total Synthesis of the Antimalarial Flindersial Alkaloids. ChemistrySelect 2016, 1 (14) , 4286-4288. https://doi.org/10.1002/slct.201601162
    79. Zhen‐Yu Tang. Anthranilic Acid–Tryptophan Alkaloids. 2016, 502-518. https://doi.org/10.1002/9781118754085.ch14
    80. Mei Xu, Rui An, Tao Huang, Xiao-jiang Hao, Sheng Liu. A biomimetic synthesis of homofascaplysin C from ditryptophans. Tetrahedron Letters 2016, 57 (11) , 1247-1249. https://doi.org/10.1016/j.tetlet.2016.02.014
    81. Nan Ji, Jiani Yuan, Shanshan Xue, Junna Zhang, Wei He. Novel chiral thiourea organocatalysts for the catalytic asymmetric oxaziridination. Tetrahedron 2016, 72 (4) , 512-517. https://doi.org/10.1016/j.tet.2015.12.010
    82. Yu Sun, Zhanchao Meng, Pengxi Chen, Deliang Zhang, Martin Baunach, Christian Hertweck, Ang Li. A concise total synthesis of sespenine, a structurally unusual indole terpenoid from Streptomyces. Organic Chemistry Frontiers 2016, 3 (3) , 368-374. https://doi.org/10.1039/C5QO00416K
    83. Kaitlin G. Henry, Lachlan M. Blair, Jonathan Sperry, Elizabeth A. Colby Davie. 4,4′-Bismoschamine: biomimetic synthesis and evidence to support structural equivalency to montamine. Organic & Biomolecular Chemistry 2016, 14 (37) , 8838-8847. https://doi.org/10.1039/C6OB01685E
    84. Shanmugam Rajasekar, Dongari Yadagiri, Pazhamalai Anbarasan. One‐Pot Aminoethylation of Indoles/Pyrroles with Alkynes and Sulfonyl Azides. Chemistry – A European Journal 2015, 21 (47) , 17079-17084. https://doi.org/10.1002/chem.201502201
    85. Cheng‐Jian Tan, Yu Zhang, Ning‐Chuan Kong, Ying‐Tong Di, Xiao‐Jiang Hao. Further Alkaloids from the Leaves of Trigonostemon lii. Helvetica Chimica Acta 2015, 98 (1) , 72-77. https://doi.org/10.1002/hlca.201400129
    86. Yu Sun, Pengxi Chen, Deliang Zhang, Martin Baunach, Christian Hertweck, Ang Li. Bioinspired Total Synthesis of Sespenine. Angewandte Chemie 2014, 126 (34) , 9158-9162. https://doi.org/10.1002/ange.201404191
    87. Yu Sun, Pengxi Chen, Deliang Zhang, Martin Baunach, Christian Hertweck, Ang Li. Bioinspired Total Synthesis of Sespenine. Angewandte Chemie International Edition 2014, 53 (34) , 9012-9016. https://doi.org/10.1002/anie.201404191
    88. M.K. Muñiz. 3.14 The Pinacol Rearrangement. 2014, 741-756. https://doi.org/10.1016/B978-0-08-097742-3.00319-0
    89. Jin-Biao Xu, Jian-Min Yue. Recent studies on the chemical constituents of Trigonostemon plants. Org. Chem. Front. 2014, 1 (10) , 1225-1252. https://doi.org/10.1039/C4QO00161C
    90. Kazuhiro Higuchi, Tomomi Kawasaki, Masato Inaba, Asuka Naganuma, Takako Ishizaki, Masanori Tayu. Hypervalent Iodine Mediated One-Pot C-H Functionalization at 2α- or 3α-Position of Indole Derivatives. HETEROCYCLES 2014, 89 (9) , 2105. https://doi.org/10.3987/COM-14-13065
    91. Thomas Buyck, Qian Wang, Jieping Zhu. Catalytic Enantioselective Michael Addition of α‐Aryl‐α‐Isocyanoacetates to Vinyl Selenone: Synthesis of α,α‐Disubstituted α‐Amino Acids and (+)‐ and (−)‐Trigonoliimine A. Angewandte Chemie 2013, 125 (48) , 12946-12950. https://doi.org/10.1002/ange.201306663
    92. Thomas Buyck, Qian Wang, Jieping Zhu. Catalytic Enantioselective Michael Addition of α‐Aryl‐α‐Isocyanoacetates to Vinyl Selenone: Synthesis of α,α‐Disubstituted α‐Amino Acids and (+)‐ and (−)‐Trigonoliimine A. Angewandte Chemie International Edition 2013, 52 (48) , 12714-12718. https://doi.org/10.1002/anie.201306663
    93. Evan D. Styduhar, Alexander D. Huters, Nicholas A. Weires, Neil K. Garg. Enantiospecific Total Synthesis of N ‐Methylwelwitindolinone D Isonitrile. Angewandte Chemie 2013, 125 (47) , 12648-12651. https://doi.org/10.1002/ange.201307464
    94. Evan D. Styduhar, Alexander D. Huters, Nicholas A. Weires, Neil K. Garg. Enantiospecific Total Synthesis of N ‐Methylwelwitindolinone D Isonitrile. Angewandte Chemie International Edition 2013, 52 (47) , 12422-12425. https://doi.org/10.1002/anie.201307464
    95. Jin‐Bao Peng, Yue Qi, Ai‐Jun Ma, Yong‐Qiang Tu, Fu‐Min Zhang, Shao‐Hua Wang, Shu‐Yu Zhang. Cascade Oxidative Dearomatization/Semipinacol Rearrangement: An Approach to 2‐Spirocyclo‐3‐oxindole Derivatives. Chemistry – An Asian Journal 2013, 8 (5) , 883-887. https://doi.org/10.1002/asia.201300032
    96. Mao Sun, Xiao-Yan Hao, Sheng Liu, Xiao-Jiang Hao. Formal synthesis of (+)-gliocladin C. Tetrahedron Letters 2013, 54 (7) , 692-694. https://doi.org/10.1016/j.tetlet.2012.12.007
    97. Jia Qiu, Jian-Xin Zhang, Sheng Liu, Xiao-Jiang Hao. A modified approach to the skeleton of trigonoliimines A and B. Tetrahedron Letters 2013, 54 (4) , 300-302. https://doi.org/10.1016/j.tetlet.2012.11.033
    98. Yogesh Goriya, Chepuri V. Ramana. Synthesis of pseudo-indoxyl derivatives via sequential Cu-catalyzed SNAr and Smalley cyclization. Chemical Communications 2013, 49 (57) , 6376. https://doi.org/10.1039/c3cc41348a
    99. B. Narendraprasad Reddy, Chepuri V. Ramana. A modular total synthesis of (±)-trigonoliimine C. Chemical Communications 2013, 49 (84) , 9767. https://doi.org/10.1039/c3cc45512b
    100. Minoru Ishikura, Takumi Abe, Tominari Choshi, Satoshi Hibino. Simple indole alkaloids and those with a non-rearranged monoterpenoid unit. Natural Product Reports 2013, 30 (5) , 694. https://doi.org/10.1039/c3np20118j
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    Cite this: J. Am. Chem. Soc. 2011, 133, 26, 10050–10053
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