6533b7cffe1ef96bd12597b4

RESEARCH PRODUCT

Synthesis of (−)-auricularic acid and its C-4 epimer the absolute configuration of auricularic acid

Miguel PeiróRamón J. ZaragozáManuel ArnóAntonio Abad

subject

StereochemistryChemistryOrganic ChemistryDrug DiscoveryAbsolute configurationEpimerBiochemistry

description

Abstract A synthesis of (−)-auricularic acid (2a) starting from methyl (+)-13-oxo- podocarp-8(14)-en-19-oate (3a) and a synthesis of its C-4 epimer (2b) starting from methyl (+)-13-oxopodocarp-8(14)-en-18-oate (3b) are described. The absolute configuration of natural auricularic acid is stablished as (4R, 5S, 8S, 9R, 10S, 14S).

https://doi.org/10.1016/s0040-4020(01)80907-8