Details

Autor(en) / Beteiligte

• Cheng, Hang
• Zhang, Zhihong
• Yao, Hongliang
• Zhang, Wei
• Yu, Jingxun
• Tong, Rongbiao

Titel

Unified Asymmetric Total Syntheses of (-)-AlotaketalsA-D and (-)-PhorbaketalA

Ist Teil von

• Angewandte Chemie International Edition, 2017-07, Vol.56 (31), p.9096

Auflage

International ed. in English

Ort / Verlag

Weinheim: Wiley Subscription Services, Inc

Erscheinungsjahr

2017

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• The novel tricyclic spiroketal alotane-type sesterterpenoids showed strikingly different biological activities and potency with subtle structural alterations. Asymmetric total syntheses of the tricyclic sesterterpenoids (-)-alotaketalsA-D and (-)-phorbaketalA were accomplished [29-31 steps from (-)-malic acid] in a collective way for the first time. The key features of the strategy included 1)a new cascade cyclization of vinyl epoxy [delta]-keto-alcohols to forge the common tricyclic spiroketal intermediate, 2)a late-stage allylic C-H oxidation, and 3)olefin cross-metathesis to install the different side chains.