Phthalide annulation: the synthesis of kalafungin, pachybasin and chrysophanolThe Journal of Organic Chemistry
Publication VersionPublished Version
AbstractThe anions of %cyano- or 3-(pheny1thio)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-(carboxymethy1)cyanohydrins. The use of phthalide anions in synthesis is exemplified by total syntheses of kalafungin, pachybasin, and chrysophanol. This methodolgy consititutes a direct and regiospecific approach to polycyclic systems.
Copyright OwnerAmerican Chemical Society
Citation InformationGeorge A. Kraus, Hidetsura Cho, Steven Crowley, Bruce Roth, et al.. "Phthalide annulation: the synthesis of kalafungin, pachybasin and chrysophanol" The Journal of Organic Chemistry Vol. 48 Iss. 20 (1983) p. 3439 - 3444
Available at: http://works.bepress.com/george_kraus/80/