Total Syntheses of Sesterterpenoid AnsellonesA and B, and Phorbadione

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, (-)-ansellonesA and B and (+)-phorbadi...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 56; no. 17; p. 4787
Main Authors Zhang, Wei, Yao, Hongliang, Yu, Jingxun, Zhang, Zhihong, Tong, Rongbiao
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 18.04.2017
EditionInternational ed. in English
Subjects
Alcohols
Anticancer properties
Antiviral activity
Epoxides
Metabolites
Nucleophiles
Oxidation
Secondary metabolites
Sesterterpenoids
Synthesis
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Summary: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, (-)-ansellonesA 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 (SN2'). 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201701879