Unified Asymmetric Total Syntheses of (−)‐Alotaketals A–D and (−)‐Phorbaketal A | Zendy

Cheng Hang | Zendy; Zhang Zhihong | Zendy; Yao Hongliang | Zendy; Zhang Wei | Zendy; Yu Jingxun | Zendy; Tong Rongbiao | Zendy

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Unified Asymmetric Total Syntheses of (−)‐Alotaketals A–D and (−)‐Phorbaketal A

Author(s) -

Cheng Hang,

Zhang Zhihong,

Yao Hongliang,

Zhang Wei,

Yu Jingxun,

Tong Rongbiao

Publication year - 2017

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201704628

Subject(s) - tricyclic , chemistry , olefin fiber , allylic rearrangement , stereochemistry , total synthesis , enantioselective synthesis , metathesis , combinatorial chemistry , organic chemistry , catalysis , polymer , polymerization

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 (−)‐alotaketals A–D and (−)‐phorbaketal A 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 δ‐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.

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