Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 1, Pages 466-469Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo8022395
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Funding
- [UCM-BSCH PR34-07-15878]
- [UCM GR74/07-910815]
- [CTQ2006-15279-C03-01]
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The chiral delta-hydroxy-gamma-butanolide moiety is widely found among biologically active natural products. We report herein the stereoselective synthesis of beta-substituted analogues of these compounds by the Rh-I-catalyzed conjugate addition of boronic acids to chiral delta-hydroxy-gamma-butenolides, easily prepared from the chiral pool. The reaction takes place with high trans diastereoselectivity without protection of the hydroxyl group. The three-step syntheses of (-)-7-oxamuricatacin (R-1 = H, R-2 = CH2-O-(C10H21)-C-n) and of new beta-substituted 7-oxamuricatacin analogues (R-1 = aryl, vinyl) is reported.
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