Volume 24, Issue 14
Natural Products
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ChemInform Abstract: Asymmetric Synthesis of 2,6-Diaminopimelic Acids.

R. M. WILLIAMS

R. M. WILLIAMS

Dep. Chem., Colorado State Univ., Fort Collins, CO 80523, USA

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C. YUAN

C. YUAN

Dep. Chem., Colorado State Univ., Fort Collins, CO 80523, USA

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First published: April 6, 1993

Abstract

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ChemInform Abstract

The commercially available chiral lactone (I) is converted to the aldehyde (IV) via the homoallyl derivative (III). (IV) is coupled with the boron enolate (VI) of (I) to give the β-hydroxy bislactone ( VII). Further transformation into the xanthogenate (X) and subsequent triphenylstannane-mediated deoxygenation produce the bislactone (XI) which is subjected to catalytic hydrogenation, yielding (R,R)-2,6- diaminopimelic acid (XII).

chemical structure image

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