Total synthesis of epothilones B and D.
[reaction: see text] A highly convergent total synthesis of the natural products epothilone B and D is described. The route is highlighted by efficient generation of a C12-C13 trisubstituted olefin which exploits a sequential Nozaki-Hiyama-Kishi coupling and a stereoselective thionyl chloride rearrangement.
Taylor
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RE
Department of Chemistry & Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556-5670, USA. taylor.61@nd.edu
Chen
Y
Y
D000475:Alkenes / Q000737:chemistry*; D001685:Biological Factors / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D034261:Epothilones; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000475:Alkenes; D001685:Biological Factors; D034261:Epothilones; D004852:Epoxy Compounds; D013844:Thiazoles; C114026:desoxyepothilone B; C093788:epothilone B