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2005
Carbohydrates
U 0500
Facially Controlled C-Methylation of Oxolanyl and Cyclopentyl Acetate Enolates:
to the Total Synthesis of (+)-Nephromopsinic Acid. — The C-methyl30- 174 Application
ation of oxolanyl and cyclopentyl acetate enolates is studied concerning the influence
of substitution pattern and configuration of the neighboring stereocenters on the
stereoselectivity of the reaction. The most important stereodirecting effect is exerted by
the bulky phenethyl group, and it is further enhanced by stereodirecting effect of a
3-O-R group. In contrast, no stereodirecting effect is observed for the endocyclic oxygen. The C-methylation reaction is applied to a highly stereoselective synthesis of
(+)-nephromopsinic acid (XIV). — (MULZER*, J.; STEFFEN, U.; MARTIN, H. J.;
ZORN, L.; Eur. J. Org. Chem. 2005, 6, 1028-1043; Inst. Org. Chem., Univ. Wien,
A-1090 Wien, Austria; Eng.) — Mischke
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