Direct Total Syntheses of Frenolicin B and Kalafungin via Highly Regioselective Diels-Alder ReactionsJournal of Organic Chemistry
Publication VersionPublished Version
AbstractFrenolicin B, an anticoccidial agent, has been synthesized in six steps from ketone 3. Racemic kalafungin, an antifungal agent, has been synthesized in five steps. The key step in both syntheses, a regioselective Diels-Alder reaction, proceeds with complete regiocontrol and in excellent yield. One rationale for the remarkable stereocontrol is that the lactone ring induces ring-puckering in the quinone subunit which, in consort with electrostatic repulsion, contributes to the regioselectivity.
Copyright OwnerAmerican Chemical Society
Citation InformationGeorge A. Kraus, Jun Li, Mark S. Gordon and Jan H. Jensen. "Direct Total Syntheses of Frenolicin B and Kalafungin via Highly Regioselective Diels-Alder Reactions" Journal of Organic Chemistry Vol. 60 Iss. 5 (1995) p. 1154 - 1159
Available at: http://works.bepress.com/george_kraus/50/