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ChemInform Abstract: Furanoterpene Synthesis via Intramolecular Nitrile Oxide Cycloaddition Reaction: A Total Synthesis of (+)-Menthofuran.
First published: April 6, 1993
Abstract
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ChemInform Abstract
The nitrile oxide derived from the chiral oxime (R)-(I), prepared from (+)-citronellal in seven steps, undergoes an intramolecular 1,3- dipolar cycloaddition reaction to form a mixture of two diastereomeric isoxazolines (II). These are subjected to alkaline hydrolysis, catalytic hydrogenation, and acidic treatment to give (+)-menthofuran ( R)-(IV).
