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Stereoselective Carbocyclization of Vinyloxiranes Catalyzed by Lewis Acids: Construction of the Musellarin Tricyclic Core
Author(s) -
Yang Sehui,
Park Euijin,
Kim Jimin
Publication year - 2021
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.12236
Subject(s) - stereoselectivity , tricyclic , lewis acids and bases , chemistry , catalysis , stereochemistry , core (optical fiber) , medicinal chemistry , organic chemistry , materials science , composite material
Stereoselective carbocyclizations of vinyloxiranes were efficiently catalyzed by Lewis acids to provide cyclic homoallyl alcohols as single isomers. The choice of Lewis acid, B(C 6 F 5 ) 3 was crucial for the stereoselective transformation in the case of cis vinyloxiranes, whereas BF 3 ∙OEt 2 was proven to be an effective catalyst for trans substrates. The method was well implemented in the synthesis of seven‐membered rings and six‐membered rings with functional group tolerance. Utility of the resulting trans ‐ and cis homoallyl alcohols was demonstrated to concisely build the tricyclic core of musellarin A and E.