Published in
American Chemical Society, Organic Letters, 7(6), p. 1139-1142, 2004
DOI: 10.1021/ol049887k
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Enantiodivergent synthesis of both enantiomers of marine alkaloids haliclorensin and isohaliclorensin, a constituent of halitulin
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- Must obtain written permission from Editor
- Must not violate ACS ethical Guidelines
- Must obtain written permission from Editor
- Must not violate ACS ethical Guidelines
Abstract
Starting from (3R)-5-benzotriazolyl-3-phenylperhydropyrido[2,1-b][1,3]oxazole 9, the enantiodivergent syntheses of both enantiomers of the marine alkaloids haliclorensin 1 and isohaliclorensin 3 have been achieved. Our syntheses feature ring-expansion reactions for the formation of the aza-macrocycle ring system of 3 and sequential ring-expansion reactions (aza-Claisen rearrangement and Zip reaction) for the formation of the aza-macrocycle ring system of 1.