jo061057s_si_001.pdf (12.4 MB)
De Novo Asymmetric Syntheses of Muricatacin and Its Analogues via Dihydroxylation of Dienoates
journal contributionposted on 2006-08-18, 00:00 authored by Md. Moinuddin Ahmed, Hu Cui, George A. O'Doherty
A short and highly efficient route to both enantiomers of muricatacin as well as the C-5-epimer has been developed. The key to the overall transformation is the highly regio- and enantioselective Sharpless asymmetric dihydroxylation of an (E,Z)-dienoate. The highly efficient stereoselective synthesis prepares (−)-muricatacin in seven steps and 66% overall yield.