Volume 28, Issue 15
Natural Products
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ChemInform Abstract: Carbonyl-Ene Approach to the Asymmetric Synthesis of 2-Keto-3-deoxy-D- gluconic Acid (KDG): A Combinatorial Sequence Using Sharpless Epoxidation.

M. SHIMIZU

M. SHIMIZU

Dep. Chem. Technol., Tokyo Inst. Technol., Meguro, Tokyo 152, Japan

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A. YOSHIDA

A. YOSHIDA

Dep. Chem. Technol., Tokyo Inst. Technol., Meguro, Tokyo 152, Japan

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K. MIKAMI

K. MIKAMI

Dep. Chem. Technol., Tokyo Inst. Technol., Meguro, Tokyo 152, Japan

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First published: 04 August 2010

Abstract

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ChemInform Abstract

The asym. approach to title acid (VIII) (in equilibrium with its furanose form) is based on the highly E-selective glyoxylate-ene reaction of the homoallyl silyl ether (I) and the asym. Sharpless epoxidation of the (E)-allylic alcohol (VI).

chemical structure image

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