Asymmetric Total Synthesis of Pyranicin
- 13 May 2009
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 11 (12) , 2695-2698
- https://doi.org/10.1021/ol900814w
Abstract
The asymmetric total synthesis of pyranicin (1) is reported. The butenolide ring was constructed via an asymmetric alkylation/ring-closing metathesis strategy. The three stereocenters in the left-hand tetrahydropyran ring were installed by sequential chiral auxiliary-mediated aldol reactions. Closure of the tetrahydropyran and fusion of the alkyl backbone were affected via a sequential ring-closing metathesis−cross-metathesis strategy.Keywords
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