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Total Syntheses of Sesterterpenoid AnsellonesA and B, and Phorbadione
Ist Teil von
Angewandte Chemie (International ed.), 2017-04, Vol.56 (17), p.4787
Auflage
International ed. in English
Ort / Verlag
Weinheim: Wiley Subscription Services, Inc
Erscheinungsjahr
2017
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
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.