Phthalide Annulation: The Synthesis of Kalafungin, Pachybasin, and Chrysophanol

George A. Kraus; Hidetsura Cho; Steven Crowley; Bruce Roth; Hirohiko Sugimoto; Susan Prugh

doi:10.1021/jo00168a013

Phthalide Annulation: The Synthesis of Kalafungin, Pachybasin, and Chrysophanol

George A. Kraus, Hidetsura Cho, Steven Crowley, Bruce Roth, Hirohiko Sugimoto, Susan Prugh

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

92 Citations (Scopus)

Abstract

The anions of 3-cyano- or 3-(phenylthio)phthalide react with Michael acceptors to afford functionalized naphthydroquinones in good yield. The cyano and phenylthio groups function both as activating groups and as leaving groups. An alternative involves the use of protected o-(carboxymethyl)cyanohydrins. The use of phthalide anions in synthesis is exemplified by total syntheses of kalafungin, pachybasin, and chrysophanol. This methodolgy constitutes a direct and regiospecific approach to polycyclic systems.

Original language	English
Pages (from-to)	3439-3444
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	48
Issue number	20
DOIs	https://doi.org/10.1021/jo00168a013
Publication status	Published - 1983 Oct
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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abstract = "The anions of 3-cyano- or 3-(phenylthio)phthalide react with Michael acceptors to afford functionalized naphthydroquinones in good yield. The cyano and phenylthio groups function both as activating groups and as leaving groups. An alternative involves the use of protected o-(carboxymethyl)cyanohydrins. The use of phthalide anions in synthesis is exemplified by total syntheses of kalafungin, pachybasin, and chrysophanol. This methodolgy constitutes a direct and regiospecific approach to polycyclic systems.",

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T2 - The Synthesis of Kalafungin, Pachybasin, and Chrysophanol

AU - Kraus, George A.

AU - Cho, Hidetsura

AU - Crowley, Steven

AU - Roth, Bruce

AU - Sugimoto, Hirohiko

AU - Prugh, Susan

PY - 1983/10

Y1 - 1983/10

N2 - The anions of 3-cyano- or 3-(phenylthio)phthalide react with Michael acceptors to afford functionalized naphthydroquinones in good yield. The cyano and phenylthio groups function both as activating groups and as leaving groups. An alternative involves the use of protected o-(carboxymethyl)cyanohydrins. The use of phthalide anions in synthesis is exemplified by total syntheses of kalafungin, pachybasin, and chrysophanol. This methodolgy constitutes a direct and regiospecific approach to polycyclic systems.

AB - The anions of 3-cyano- or 3-(phenylthio)phthalide react with Michael acceptors to afford functionalized naphthydroquinones in good yield. The cyano and phenylthio groups function both as activating groups and as leaving groups. An alternative involves the use of protected o-(carboxymethyl)cyanohydrins. The use of phthalide anions in synthesis is exemplified by total syntheses of kalafungin, pachybasin, and chrysophanol. This methodolgy constitutes a direct and regiospecific approach to polycyclic systems.

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Phthalide Annulation: The Synthesis of Kalafungin, Pachybasin, and Chrysophanol

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