[3+ 2] Cycloaddition of Nonstabilized Azomethine Ylides. 7. Stereoselective Synthesis of Epibatidine and Analogues
G Pandey, TD Bagul, AK Sahoo
Index: Pandey, Ganesh; Bagul, Trusar D.; Sahoo, Akhil K. Journal of Organic Chemistry, 1998 , vol. 63, # 3 p. 760 - 768
Full Text: HTML
Citation Number: 92
Abstract
Epibatidine (1) is synthesized by employing a [3+ 2] cycloaddition strategy as a key step via nonstabilized azomethine ylide 10, generated by one-electron oxidative double desilylation of N-benzyl-2, 5-bis (trimethylsilyl) pyrrolidine (12). Cycloaddition of 10 with trans-ethyl-3-(6- chloro-3-pyridyl)-2-propenoate (22a) gives 26 in which the 6-chloro-3-pyridyl moiety is endo- oriented. Decarboxylation followed by debenzylation gives unnatural epimer 30 of 1. The ...
Related Articles:
[Na, Youngim; Park, Soyoung; Han, Soo Bong; Han, Hoon; Ko, Sangwon; Chang, Sukbok Journal of the American Chemical Society, 2004 , vol. 126, # 1 p. 250 - 258]
[Otrubova, Katerina; Cravatt, Benjamin F.; Boger, Dale L. Journal of Medicinal Chemistry, 2014 , vol. 57, # 3 p. 1079 - 1089]
Synthesis and antifungal activities of R-102557 and related dioxane-triazole derivatives.
[Chemical and Pharmaceutical Bulletin, , vol. 48, # 5 p. 694 - 707]
[Journal of Medicinal Chemistry, , vol. 57, # 3 p. 1079 - 1089]
Synthesis and antifungal activities of R-102557 and related dioxane-triazole derivatives.
[Chemical and Pharmaceutical Bulletin, , vol. 48, # 5 p. 694 - 707]