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Total Syntheses of Sesterterpenoid Ansellones A and B, and Phorbadione
Ist Teil von
Angewandte Chemie (International ed.), 2017-04, Vol.56 (17), p.4787-4791
Ort / Verlag
Germany
Erscheinungsjahr
2017
Link zum Volltext
Quelle
MEDLINE
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, (−)‐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 (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.
Minding manners: Unusual regioselective intramolecular cyclization of 1,3‐cyclohexadiene epoxides with alcohol nucleophiles in a 1,4‐addition manner enabled the first asymmetric total syntheses of (−)‐ansellones A and B and (+)‐phorbadione in 16–23 steps from (+)‐sclareolide. This strategy is expected to be applicable to the synthesis of other ansellane sesterterpenoids.