Toward a total synthesis of peloruside A: enantioselective preparation of the C8-C19 region.
An efficient synthetic sequence toward the C8-C19 region of peloruside A has been developed. The route is highlighted by a selective electrophilic cyclization reaction, a single-step epoxide ring-opening/methylation sequence, and a stereoselective Mukaiyama aldol reaction. [reaction: see text]
Taylor
Richard E
RE
Department of Chemistry and Biochemistry and the Walther Cancer Research Center, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556-5670, USA. taylor.61@nd.edu
Jin
Meizhong
M
D000478:Alkylation; D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D011161:Porifera; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; D007783:Lactones; C414085:peloruside A