A New Strategy toward the Total Synthesis of Stachyflin, A Potent Anti-Influenza A Virus Agent: Concise Route to the Tetracyclic Core Structure

Organic Letters

Volumn 4, Issue 25, 2002, Pages 4483-4486

  Nakatani, Mari ^a   Nakamura, Masahiko ^a,b   Suzuki, Akiyuki ^a,c   Inoue, Munenori ^a   Katoh, Tadashi ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^c KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; SESQUITERPENE; STACHYFLIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; INFLUENZA VIRUS A; STACHYBOTRYS; SYNTHESIS;

ANTIVIRAL AGENTS; CYCLIZATION; INFLUENZA A VIRUS; MOLECULAR STRUCTURE; SESQUITERPENES; STACHYBOTRYS;

EID: 0037069714     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0271032     Document Type: Article

References (26)

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18. This type of reductive alkylation, originally developed by Stork et al. in the 1960s, has been widely utilized as a critical step in the total synthesis of marine sesquiterpene quinones and hydroquinones. For recent examples, see: (a) Ling, T.; Poupon, E.; Rueden, E. J.; Kim, S. H.; Theodorakis, E. A. J. Am. Chem. Soc. 2002, 124, 12261. (b) Stahl, P.; Kissau, L.; Mazitschek, R.; Huwe, A.; Furet, P.; Giannis, A.; Waldmann, H. J. Am. Chem. Soc. 2001, 123, 11586. Poigny, S.; Guyot, M.; Samadi, M. J. Org. Chem. 1998, 63, 5890. Locke, E. P.; Hecht, S. M. Chem. Commun. 1996, 2717. (e) An, J.; Wiemer, D. F. J. Org. Chem. 1996, 61, 8775. (f) Bruner, S. D.; Radeke, H. S.; Tallarico, J. A.; Snapper, M. L. J. Org. Chem. 1995, 60, 1114. (g) Sarma, A. S.; Chattopadhyay, P. J. Org. Chem. 1982, 47, 1727.
19. This type of reductive alkylation, originally developed by Stork et al. in the 1960s, has been widely utilized as a critical step in the total synthesis of marine sesquiterpene quinones and hydroquinones. For recent examples, see: (a) Ling, T.; Poupon, E.; Rueden, E. J.; Kim, S. H.; Theodorakis, E. A. J. Am. Chem. Soc. 2002, 124, 12261. (b) Stahl, P.; Kissau, L.; Mazitschek, R.; Huwe, A.; Furet, P.; Giannis, A.; Waldmann, H. J. Am. Chem. Soc. 2001, 123, 11586. (C) Poigny, S.; Guyot, M.; Samadi, M. J. Org. Chem. 1998, 63, 5890. Locke, E. P.; Hecht, S. M. Chem. Commun. 1996, 2717. (e) An, J.; Wiemer, D. F. J. Org. Chem. 1996, 61, 8775. (f) Bruner, S. D.; Radeke, H. S.; Tallarico, J. A.; Snapper, M. L. J. Org. Chem. 1995, 60, 1114. (g) Sarma, A. S.; Chattopadhyay, P. J. Org. Chem. 1982, 47, 1727.
20. This type of reductive alkylation, originally developed by Stork et al. in the 1960s, has been widely utilized as a critical step in the total synthesis of marine sesquiterpene quinones and hydroquinones. For recent examples, see: (a) Ling, T.; Poupon, E.; Rueden, E. J.; Kim, S. H.; Theodorakis, E. A. J. Am. Chem. Soc. 2002, 124, 12261. (b) Stahl, P.; Kissau, L.; Mazitschek, R.; Huwe, A.; Furet, P.; Giannis, A.; Waldmann, H. J. Am. Chem. Soc. 2001, 123, 11586. Poigny, S.; Guyot, M.; Samadi, M. J. Org. Chem. 1998, 63, 5890. (d) Locke, E. P.; Hecht, S. M. Chem. Commun. 1996, 2717. (e) An, J.; Wiemer, D. F. J. Org. Chem. 1996, 61, 8775. (f) Bruner, S. D.; Radeke, H. S.; Tallarico, J. A.; Snapper, M. L. J. Org. Chem. 1995, 60, 1114. (g) Sarma, A. S.; Chattopadhyay, P. J. Org. Chem. 1982, 47, 1727.
21. This type of reductive alkylation, originally developed by Stork et al. in the 1960s, has been widely utilized as a critical step in the total synthesis of marine sesquiterpene quinones and hydroquinones. For recent examples, see: (a) Ling, T.; Poupon, E.; Rueden, E. J.; Kim, S. H.; Theodorakis, E. A. J. Am. Chem. Soc. 2002, 124, 12261. (b) Stahl, P.; Kissau, L.; Mazitschek, R.; Huwe, A.; Furet, P.; Giannis, A.; Waldmann, H. J. Am. Chem. Soc. 2001, 123, 11586. Poigny, S.; Guyot, M.; Samadi, M. J. Org. Chem. 1998, 63, 5890. Locke, E. P.; Hecht, S. M. Chem. Commun. 1996, 2717. (e) An, J.; Wiemer, D. F. J. Org. Chem. 1996, 61, 8775. (f) Bruner, S. D.; Radeke, H. S.; Tallarico, J. A.; Snapper, M. L. J. Org. Chem. 1995, 60, 1114. (g) Sarma, A. S.; Chattopadhyay, P. J. Org. Chem. 1982, 47, 1727.
22. This type of reductive alkylation, originally developed by Stork et al. in the 1960s, has been widely utilized as a critical step in the total synthesis of marine sesquiterpene quinones and hydroquinones. For recent examples, see: (a) Ling, T.; Poupon, E.; Rueden, E. J.; Kim, S. H.; Theodorakis, E. A. J. Am. Chem. Soc. 2002, 124, 12261. (b) Stahl, P.; Kissau, L.; Mazitschek, R.; Huwe, A.; Furet, P.; Giannis, A.; Waldmann, H. J. Am. Chem. Soc. 2001, 123, 11586. Poigny, S.; Guyot, M.; Samadi, M. J. Org. Chem. 1998, 63, 5890. Locke, E. P.; Hecht, S. M. Chem. Commun. 1996, 2717. (e) An, J.; Wiemer, D. F. J. Org. Chem. 1996, 61, 8775. (f) Bruner, S. D.; Radeke, H. S.; Tallarico, J. A.; Snapper, M. L. J. Org. Chem. 1995, 60, 1114. (g) Sarma, A. S.; Chattopadhyay, P. J. Org. Chem. 1982, 47, 1727.
23. This type of reductive alkylation, originally developed by Stork et al. in the 1960s, has been widely utilized as a critical step in the total synthesis of marine sesquiterpene quinones and hydroquinones. For recent examples, see: (a) Ling, T.; Poupon, E.; Rueden, E. J.; Kim, S. H.; Theodorakis, E. A. J. Am. Chem. Soc. 2002, 124, 12261. (b) Stahl, P.; Kissau, L.; Mazitschek, R.; Huwe, A.; Furet, P.; Giannis, A.; Waldmann, H. J. Am. Chem. Soc. 2001, 123, 11586. Poigny, S.; Guyot, M.; Samadi, M. J. Org. Chem. 1998, 63, 5890. Locke, E. P.; Hecht, S. M. Chem. Commun. 1996, 2717. (e) An, J.; Wiemer, D. F. J. Org. Chem. 1996, 61, 8775. (f) Bruner, S. D.; Radeke, H. S.; Tallarico, J. A.; Snapper, M. L. J. Org. Chem. 1995, 60, 1114. (g) Sarma, A. S.; Chattopadhyay, P. J. Org. Chem. 1982, 47, 1727.
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25. When ethylene acetal 10 was used as a substrate for this hydrogenation under the same reaction conditions, a considerable decrease in the stereoselectivity at C8 was observed (β-Me:α-Me = ca. 2:1); this is probably due to an unfavorable conformation of the decalin ring. For similar examples of this phenomenon, see ref 13b,c,d,e.
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