Chemistry, Ames Laboratory
Journal or Book Title
The Journal of Organic Chemistry
Frenolicin 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.
American Chemical Society
Kraus, George A.; Li, Jun; Gordon, Mark S.; and Jensen, Jan H., "Direct Total Syntheses of Frenolicin B and Kalafungin via Highly Regioselective Diels-Alder Reactions" (1995). Chemistry Publications. 627.