The Isoxazoline Route to the Hypocholesterolemic Agent Compactin: Use of the Isoxazoline as a 1,3-Diene Equivalent

Alan P. Kozikowski; Chun sing Li

doi:10.1021/jo00392a009

The Isoxazoline Route to the Hypocholesterolemic Agent Compactin: Use of the Isoxazoline as a 1,3-Diene Equivalent

Alan P. Kozikowski, Chun sing Li

School of Medicine

Research output: Contribution to journal › Article › peer-review

44 Scopus citations

Abstract

A total synthesis of the hypocholesterolemic agent compactin is described in which the hexahydronaphthalene portion of this molecule is constructed by an intramolecular nitrile oxide cycloaddition reaction. In the context of this synthesis, the isoxazoline ring system was found to serve as a useful 1,3-diene equivalent. The protocol developed for this conversion involves transformation of the isoxazoline to an allylic alcohol followed by regioselective dehydration using aluminum oxide. Molecular mechanics calculations on compactin-related octahydro-naphthisoxazoles are also presented.

Original language	English (US)
Pages (from-to)	3541-3552
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	52
Issue number	16
DOIs	https://doi.org/10.1021/jo00392a009
State	Published - Aug 1 1987

ASJC Scopus subject areas

Organic Chemistry

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abstract = "A total synthesis of the hypocholesterolemic agent compactin is described in which the hexahydronaphthalene portion of this molecule is constructed by an intramolecular nitrile oxide cycloaddition reaction. In the context of this synthesis, the isoxazoline ring system was found to serve as a useful 1,3-diene equivalent. The protocol developed for this conversion involves transformation of the isoxazoline to an allylic alcohol followed by regioselective dehydration using aluminum oxide. Molecular mechanics calculations on compactin-related octahydro-naphthisoxazoles are also presented.",

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AB - A total synthesis of the hypocholesterolemic agent compactin is described in which the hexahydronaphthalene portion of this molecule is constructed by an intramolecular nitrile oxide cycloaddition reaction. In the context of this synthesis, the isoxazoline ring system was found to serve as a useful 1,3-diene equivalent. The protocol developed for this conversion involves transformation of the isoxazoline to an allylic alcohol followed by regioselective dehydration using aluminum oxide. Molecular mechanics calculations on compactin-related octahydro-naphthisoxazoles are also presented.

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The Isoxazoline Route to the Hypocholesterolemic Agent Compactin: Use of the Isoxazoline as a 1,3-Diene Equivalent

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