Intramolecular nitrile oxide cycloaddition route to carbocyclics: A formal total synthesis of PGF2α

Alan P. Kozikowski; Philip D. Stein

doi:10.1021/jo00187a001

Intramolecular nitrile oxide cycloaddition route to carbocyclics: A formal total synthesis of PGF_2α

Alan P. Kozikowski, Philip D. Stein

School of Medicine

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Abstract

A formal total synthesis of the prostaglandin F_2α is reported which is based on the reaction of a nitrile oxide, generated by the sodium hypochlorite oxidation of an oxime, with a tethered olefin. The present study reveals the importance of an existing ring structure to control both the kinetics and the stereochemical course of the cycloaddition process. The possibility of carrying out the present synthesis in a chiral-selective fashion through employment of a chiral epoxide is also discussed.

Original language	English (US)
Pages (from-to)	2301-2309
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	49
Issue number	13
DOIs	https://doi.org/10.1021/jo00187a001
State	Published - Jan 1984

ASJC Scopus subject areas

Organic Chemistry

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title = "Intramolecular nitrile oxide cycloaddition route to carbocyclics: A formal total synthesis of PGF2α",

abstract = "A formal total synthesis of the prostaglandin F2α is reported which is based on the reaction of a nitrile oxide, generated by the sodium hypochlorite oxidation of an oxime, with a tethered olefin. The present study reveals the importance of an existing ring structure to control both the kinetics and the stereochemical course of the cycloaddition process. The possibility of carrying out the present synthesis in a chiral-selective fashion through employment of a chiral epoxide is also discussed.",

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year = "1984",

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AU - Stein, Philip D.

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N2 - A formal total synthesis of the prostaglandin F2α is reported which is based on the reaction of a nitrile oxide, generated by the sodium hypochlorite oxidation of an oxime, with a tethered olefin. The present study reveals the importance of an existing ring structure to control both the kinetics and the stereochemical course of the cycloaddition process. The possibility of carrying out the present synthesis in a chiral-selective fashion through employment of a chiral epoxide is also discussed.

AB - A formal total synthesis of the prostaglandin F2α is reported which is based on the reaction of a nitrile oxide, generated by the sodium hypochlorite oxidation of an oxime, with a tethered olefin. The present study reveals the importance of an existing ring structure to control both the kinetics and the stereochemical course of the cycloaddition process. The possibility of carrying out the present synthesis in a chiral-selective fashion through employment of a chiral epoxide is also discussed.

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Intramolecular nitrile oxide cycloaddition route to carbocyclics: A formal total synthesis of PGF_2α

Abstract

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