TOTAL SYNTHESIS OF d,l-LONGIFOLENE

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2. Robert F. Lusi, Goh Sennari, Richmond Sarpong. Strategy Evolution in a Skeletal Remodeling and C–H Functionalization-Based Synthesis of the Longiborneol Sesquiterpenoids. Journal of the American Chemical Society 2022, 144 (37) , 17277-17294. https://doi.org/10.1021/jacs.2c08136
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4. Markus D. Kärkäs, John A. Porco, Jr., and Corey R. J. Stephenson . Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis. Chemical Reviews 2016, 116 (17) , 9683-9747. https://doi.org/10.1021/acs.chemrev.5b00760
5. Steven J. McKerrall, Lars Jørgensen, Christian A. Kuttruff, Felix Ungeheuer, and Phil S. Baran . Development of a Concise Synthesis of (+)-Ingenol. Journal of the American Chemical Society 2014, 136 (15) , 5799-5810. https://doi.org/10.1021/ja501881p
6. Terry P. Lebold, Gary M. Gallego, Christopher J. Marth, and Richmond Sarpong . Synthesis of the Bridging Framework of Phragmalin-Type Limonoids. Organic Letters 2012, 14 (8) , 2110-2113. https://doi.org/10.1021/ol300647k
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9. Bo Yin, Xiaohuan Li, Zi‐Xiang Li, Xiao‐Xin Zhu, Lan Zhang, Xian‐Li Zhou, Jin‐Bu Xu, Feng‐Zheng Chen, Pei Tang, Feng Gao. Adenophorone, An Unprecedented Sesquiterpene from Eupatorium adenophorum : Structural Elucidation, Bioinspired Total Synthesis and Neuroprotective Activity Evaluation. Angewandte Chemie 2023, 135 (31) https://doi.org/10.1002/ange.202306326
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11. Robert F. Lusi, Goh Sennari, Richmond Sarpong. Total synthesis of nine longiborneol sesquiterpenoids using a functionalized camphor strategy. Nature Chemistry 2022, 14 (4) , 450-456. https://doi.org/10.1038/s41557-021-00870-4
12. J. Polanski. Chemoinformatics. 2020, 635-676. https://doi.org/10.1016/B978-0-12-409547-2.14327-6
13. Dharmesh Harwani, Jyotsna Begani, Jyoti Lakhani. Genes to Metabolites and Metabolites to Genes Approaches to Predict Biosynthetic Pathways in Microbes for Natural Product Discovery. 2018, 1-16. https://doi.org/10.1007/978-981-13-0347-0_1
14. Niko S. Radulović, Milan S. Nešić. Diverse acetals from stoichiometric amounts of aldehydes and alcohols under very mild conditions: a new twist to PPh 3 –CCl 4 reagent combination. RSC Advances 2016, 6 (95) , 93068-93080. https://doi.org/10.1039/C6RA19980A
15. Surendar Reddy Bathula, Srirama Murthy Akondi, Prathama S. Mainkar, Srivari Chandrasekhar. “Pruning of biomolecules and natural products (PBNP)”: an innovative paradigm in drug discovery. Organic & Biomolecular Chemistry 2015, 13 (23) , 6432-6448. https://doi.org/10.1039/C5OB00403A
16. Leandro de C. Alves, André L. Desiderá, Kleber T. de Oliveira, Sean Newton, Steven V. Ley, Timothy J. Brocksom. A practical deca-gram scale ring expansion of (R)-(−)-carvone to (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1. Organic & Biomolecular Chemistry 2015, 13 (28) , 7633-7642. https://doi.org/10.1039/C5OB00525F
17. Erik J. Sorensen, David A. Siler, Jeffrey D. Mighion. Taking Risks in Complex Synthesis Design. 2013, 249-273. https://doi.org/10.1016/B978-0-08-099362-1.00009-6
18. Jonathan William Medley, Mohammad Movassaghi. Robinson's landmark synthesis of tropinone. Chemical Communications 2013, 49 (92) , 10775. https://doi.org/10.1039/c3cc44461a
19. Anthony Cook, A. Peter Johnson, James Law, Mahdi Mirzazadeh, Orr Ravitz, Aniko Simon. Computer‐aided synthesis design: 40 years on. WIREs Computational Molecular Science 2012, 2 (1) , 79-107. https://doi.org/10.1002/wcms.61
20. . Large‐Ring Carbocycles. 2010, 423-588. https://doi.org/10.1002/9780470872215.ch5
21. J. Polanski. Chemoinformatics. 2009, 459-506. https://doi.org/10.1016/B978-044452701-1.00006-5
22. Gopal Subramaniam, Varsha Patel, Sasan Karimi. Conformational Analysis of Longifolene. Spectroscopy Letters 2008, 41 (7) , 349-353. https://doi.org/10.1080/00387010802371528
23. Fayang Qiu. Strategic efficiency — The new thrust for synthetic organic chemists. Canadian Journal of Chemistry 2008, 86 (9) , 903-906. https://doi.org/10.1139/v08-120
24. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Calcium Carbonate. 2006https://doi.org/10.1002/9780471264194.fos02171
25. Gopal Subramaniam, Sasan Karimi, David Phillips. Solution conformation of longifolene and its precursor by NMR and ab initio calculations. Magnetic Resonance in Chemistry 2006, 44 (12) , 1118-1121. https://doi.org/10.1002/mrc.1908
26. Vladimir Dimitrov, Gudrun Hopp Rentsch, Anthony Linden, Manfred Hesse. The Ozonolysis of Longifolene: A Tool for the Preparation of Useful Chiral Compounds. Configuration Determination of New Stereogenic Centers by NMR Spectroscopy and X‐Ray Crystallography. Helvetica Chimica Acta 2003, 86 (1) , 106-121. https://doi.org/10.1002/hlca.200390000
27. Francesco Pietra. The role of chemical synthesis. 2002, 215-265. https://doi.org/10.1016/S1460-1567(02)80024-1
28. . References. 2002, 305-345. https://doi.org/10.1016/S1460-1567(02)80027-7
29. Eric J. Kantorowski, Mark J. Kurth. Expansion to Seven-Membered Rings. Tetrahedron 2000, 56 (26) , 4317-4353. https://doi.org/10.1016/S0040-4020(00)00218-0
30. K. C. Nicolaou, Dionisios Vourloumis, Nicolas Winssinger, Phil S. Baran. Der Stand der Totalsynthese zu Beginn des 21. Jahrhunderts. Angewandte Chemie 2000, 112 (1) , 46-126. https://doi.org/10.1002/(SICI)1521-3757(20000103)112:1<46::AID-ANGE46>3.0.CO;2-P
31. Clayton H. Heathcock. Die faszinierenden Alkaloide aus Yuzuriha. Angewandte Chemie 1992, 104 (6) , 675-691. https://doi.org/10.1002/ange.19921040604
32. Clayton H. Heathcock. The Enchanting Alkaloids of Yuzuriha. Angewandte Chemie International Edition in English 1992, 31 (6) , 665-681. https://doi.org/10.1002/anie.199206653
33. Elias James Corey. Die Logik der chemischen Synthese: Vielstufige Synthesen komplexer „carbogener”︁ Moleküle (Nobel‐Vortrag). Angewandte Chemie 1991, 103 (5) , 469-479. https://doi.org/10.1002/ange.19911030504
34. Elias James Corey. The Logic of Chemical Synthesis: Multistep Synthesis of Complex Carbogenic Molecules (Nobel Lecture). Angewandte Chemie International Edition in English 1991, 30 (5) , 455-465. https://doi.org/10.1002/anie.199104553
35. P. Pfeifer, J. Mulzer, A. Müller, M. Penk, A. Heintz, G. Reinbendt, H. Parlar, Klaus Roth, D. Henschler, Ulrich Schindeuoff. mini‐chiuz. Chemie in unserer Zeit 1990, 24 (6) , 254-266. https://doi.org/10.1002/ciuz.19900240602
36. Sukh Dev. The Chemistry of Longifolene and Its Derivatives. 1981, 49-104. https://doi.org/10.1007/978-3-7091-8611-4_2
37. Clayton H. Heathcock. Total Synthesis of Sequiterpenes. 1973, 197-558. https://doi.org/10.1002/9780470129654.ch2
38. William Tubiana, Bernard Waegell. Synthesis of 7,7‐Dimethylbicyclo[4.1.1]octan‐3‐one by Pinacolic Rearrangement. Angewandte Chemie International Edition in English 1972, 11 (7) , 640-641. https://doi.org/10.1002/anie.197206402
39. William Tubiana, Bernard Waegell. Synthese von 7,7‐Dimethyl‐bicyclo[4.1.1]octan‐3‐on durch Pinakol‐Umlagerung. Angewandte Chemie 1972, 84 (13) , 642-643. https://doi.org/10.1002/ange.19720841310
40. J. Lhomme, G. Ourisson. Le longifolène—XIV. Tetrahedron 1968, 24 (8) , 3177-3200. https://doi.org/10.1016/S0040-4020(01)92617-1
41. A. K. Sen Gupta. Einige neue Derivate des Cafestols, eines Diterpens aus der Kaffeebohne. Fette, Seifen, Anstrichmittel 1964, 66 (12) , 1056-1059. https://doi.org/10.1002/lipi.19640661219
42. R. Ivor Reed. Mass Spectra of Terpenes. 1963, 637-699. https://doi.org/10.1016/B978-0-12-395620-0.50017-7
43. H. A. P. de Jongh, Hans Wynberg. Synthesis of spirocyclic compounds by the intramolecular michael reaction. Recueil des Travaux Chimiques des Pays-Bas 1963, 82 (2) , 202-212. https://doi.org/10.1002/recl.19630820213
44. P. Narasimha Rao, H.R. Gollberg. Raney nickel desulfurization of 19-norsteroid ethylenethioketals. Tetrahedron 1962, 18 (11) , 1251-1256. https://doi.org/10.1016/0040-4020(62)80006-4