- Total synthesis and revision of the absolute configuration of seimatopolide B.
Total synthesis and revision of the absolute configuration of seimatopolide B.
Organic & biomolecular chemistry (2013-04-09)
Chada Raji Reddy, Uredi Dilipkumar, Motatipally Damoder Reddy, Nagavaram Narsimha Rao
PMID23563244
ABSTRACT
The asymmetric total synthesis of natural seimatopolide B along with its enantiomer is described starting from readily available 5-hexen-1-ol and 3-buten-1-ol. The key steps involved are Jacobson hydrolytic kinetic resolution, proline-catalyzed α-hydroxylation, Yamaguchi esterification and ring-closing metathesis. This asymmetric total synthesis necessitates the revision of the originally assigned (3R, 6S, 9S)-configuration to (3S, 6R, 9R).