Journal of Organic Chemistry 2001-06-01

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

M Hartl, H U Humpf

Index: J. Org. Chem. 66(11) , 3678-81, (2001)

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Abstract

The circular dichroism (CD) exciton chirality method was employed for the stereochemical assignment of the tricarballylic acid (TCA) side chains of fumonisin B(1) 1a (FB(1)). Using 2-naphthoate for chromophoric derivatization of the reduced TCA moieties, the absolute configuration was shown to be R. For additional confirmation, an optically active dihydroxy-tert-butanoate 2 related to the TCA group of fumonisin B(1) was synthesized to serve as a model compound.