SYNTHESIS OF BETA-DIMORPHECOLIC ACID EXPLOITING HIGHLY STEREOSELECTIVE REDUCTION OF A SIDE-CHAIN CARBONYL GROUP IN A PI-ALLYLTRICARBONYLIRON LACTONE COMPLEX

Authors
LEY SV MEEK G
Citation
Sv. Ley et G. Meek, SYNTHESIS OF BETA-DIMORPHECOLIC ACID EXPLOITING HIGHLY STEREOSELECTIVE REDUCTION OF A SIDE-CHAIN CARBONYL GROUP IN A PI-ALLYLTRICARBONYLIRON LACTONE COMPLEX, Journal of the Chemical Society. Perkin transactions. I, (8), 1997, pp. 1125-1133
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
8
Year of publication
1997
Pages
1125 - 1133
Database
ISI
SICI code
0300-922X(1997):8<1125:SOBAEH>2.0.ZU;2-N
Abstract
A highly enantioselective synthesis of beta-dimorphecolic acid 1 is re ported. The synthesis features a diastereoselective reduction of the k etone 4, in which the tricarbonyliron lactone tether induces a 1,5 tra nsfer of chirality, followed by a stereoselective decarboxylation to c reate all the stereochemical elements of 1. Selective oxidation of the primary alcohol in the diol 17 serves to introduce the acid functiona lity.