Enantioselective synthesis of the predominant AB ring system of the Schisandra nortriterpenoid natural products
- PMID: 25126673
- DOI: 10.1021/ol502027m
Enantioselective synthesis of the predominant AB ring system of the Schisandra nortriterpenoid natural products
Abstract
An enantioselective synthesis of the AB ring system common to the majority of the Schisandra nortriterpenoid natural products is reported. Key steps include a stereospecific ring opening of a trisubstituted epoxide and the use of a β-lactone to enable installation of the gem-dimethyl functionality of the B ring. An acetalization strategy played a key role in a late-stage biomimetic AB ring bicyclization.
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