Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 17, Pages 4787-4791Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201701879
Keywords
cyclizations; natural products; structure determination; terpenoids; total synthesis
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Funding
- Research Grant Council of Hong Kong [ECS 605912, GRF 605113, GRF 16305314, GRF 16311716]
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Ansellane-type sesterterpenoids including, ansellones A-G and (+)-phorbadione are structurally novel marine secondary metabolites which exhibit anticancer and anti-HIV activity. The first, asymmetric total syntheses of three structurally representative members, (-)-ansellones A and B and (+)-phorbadione, were accomplished in 16-23 steps from (+)-sclareolide. The route features the first regioselective cyclization of vinyl epoxides with internal alcohol nucleophiles in a 1,4-addition manner (S(N)2'). Additionally, the allylic C-H oxidation was exploited at a late stage of the synthesis of (-)-ansellone A and (+)-phorbadione. This strategy is expected to be applicable to the synthesis of other ansellane sesterterpenoids.
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