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Enantioselective Synthesis of 10-epi-Anamarine via an Iterative Dihydroxylation Sequence

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journal contribution
posted on 17.03.2005, 00:00 by Dong Gao, George A. O'Doherty
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 α,β-unsaturated lactones.