Use of aziridines for the stereocontrolled synthesis of (-)-LL-C10037α, (+)-MT35214, and (+)-4-epi-MT35214

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Abstract

Strategies for the synthesis of the title compounds have been developed using a diastereoselective aziridination reaction of 4-O-substituted cyclohexenones. Aziridination using a chiral amine permitted resolution of a 4-hydroxycyclohexane derivative, and this resulted in the synthesis of both enantiomers of the title compound. Alternatively, the chiral 4-hydroxycyclohexenone starting material was derived from quinic acid. In both cases stereoselective epoxidation and opening of the aziridine ring with hydrazoic acid afforded the 2-azidocyclohexenone, which was transformed to the 2-acetamido group present in the natural product.

Original languageEnglish
Pages (from-to)1929-1937
Number of pages9
JournalJournal of Organic Chemistry
Volume79
Issue number5
DOIs
Publication statusPublished - 7 Mar 2014

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