Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 30, Pages 6401-6410Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob01217a
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- CSIR, New Delhi [02(0184)/14/EMR-II]
- UGC
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An expedient synthetic approach has been developed for the unified total synthesis of (+)-chinensiolide B and (+)-8-epigrosheimin. The point of divergence was provided by the lactone aldehyde 6, in which four contiguous stereocenters were achieved by a stereocontrolled Evans syn-aldol reaction of a R-carvone derived enantiopure aldehyde and chiral N-succinyl-oxazolidinone. The lactone aldehyde 6 was synthesized in multigram quantity in three steps. Highly optimized chemo-and stereoselective reactions and functional group interconversion enabled us to assemble (+)-chinensiolide B and (+)-8-epigrosheimin from 6.
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