Combined synthetic/CD strategy for the stereochemical assignment of the tricarballylic acid side chains of fumonisin B-1

Authors
Hartl, M Humpf, HU
Citation
M. Hartl et Hu. Humpf, Combined synthetic/CD strategy for the stereochemical assignment of the tricarballylic acid side chains of fumonisin B-1, J ORG CHEM, 66(11), 2001, pp. 3678-3681
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
11
Year of publication
2001
Pages
3678 - 3681
Database
ISI
SICI code
0022-3263(20010601)66:11<3678:CSSFTS>2.0.ZU;2-D
Abstract
The circular dichroism (CD) exciton chirality method was employed for the s tereochemical assignment of the tricarballylic acid (TCA) side chains of fu monisin B-1 1a (FB1). Using 2-naphthoate for chromophoric derivatization of the reduced TCA moieties, the absolute configuration was shown to be R. Fo r additional confirmation, an optically active dihydroxy-tert-butanoate 2 r elated to the TCA group of fumonisin BI was synthesized to serve as a model compound.