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. 2005 Mar 17;7(6):1069-72.
doi: 10.1021/ol047322i.

Enantioselective synthesis of 10-epi-anamarine via an iterative dihydroxylation sequence

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Enantioselective synthesis of 10-epi-anamarine via an iterative dihydroxylation sequence

Dong Gao et al. Org Lett. .

Abstract

[reaction: see text] The enantioselective syntheses of 10-epi-anamarine and 5,10-epi,epi-anamarine have been achieved in 13 to 14 steps. The route relies upon an enantio- and regioselective Sharpless dihydroxylation of either dienoates or trienoates to establish the C-8 to C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route also relies upon a ring-closing metathesis to establish the alpha,beta-unsaturated lactones.

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