Enantioselective synthesis of 10-epi-anamarine via an iterative dihydroxylation sequence |
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Authors: | Gao Dong O'Doherty George A |
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Affiliation: | Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA. |
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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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