A short total synthesis of (+)-omaezakianol via an epoxide-initiated cationic cascade reaction.
(+)-Omaezakianol was synthesized in only three steps from racemic chlorohydrin 4 by Shi epoxidation followed by cascade cyclization and reduction.
Xiong
Zhaoming
Z
Department of Medicinal Chemistry, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, Connecticut 06877, USA. zhaoming.xiong@boehringer-ingelheim.com
Busch
Robert
R
Corey
E J
EJ
D002412:Cations / Q000737:chemistry; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D013185:Squalene / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D002412:Cations; D004852:Epoxy Compounds; C540153:omaezakianol; D013185:Squalene