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. 2005 Nov 25;70(24):9932-9.
doi: 10.1021/jo051681p.

De novo asymmetric synthesis of anamarine and its analogues

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De novo asymmetric synthesis of anamarine and its analogues

Dong Gao et al. J Org Chem. .

Abstract

[reaction: see text] The enantioselective synthesis of anamarine has been achieved in 21 steps. The route relies on enantio- and regioselective Sharpless dihydroxylation of dienoate ester and zinc borohydride reduction to establish the C-8-C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route has also been used to prepare two diastereoisomers of anamarine in 14 steps.

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