Synthesis of asymmetrically-substituted cyclopentane derivatives from acyclic sugars

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Abstract
Diels–Alder addition of cyclopentadiene and trans-α,β-unsaturated sugar derivatives proceeds with high steric control to afford crystalline, optically pure norbornene derivatives that may be transformed into tetra-C-substituted cyclopentane derivatives of defined stereochemistry at all four centres; the products are of interest in synthesis of prostaglandin analogues.

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