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. 2014 Sep 5;16(17):4480-3.
doi: 10.1021/ol502027m. Epub 2014 Aug 15.

Enantioselective synthesis of the predominant AB ring system of the Schisandra nortriterpenoid natural products

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Enantioselective synthesis of the predominant AB ring system of the Schisandra nortriterpenoid natural products

Birgit Gockel et al. Org Lett. .

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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