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 journalArticlepeer-review

94 Citations (Scopus)


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 languageEnglish
Pages (from-to)3439-3444
Number of pages6
JournalJournal of Organic Chemistry
Issue number20
Publication statusPublished - 1983 Oct
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry


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