Feldman KS,
*,
Mechem CC,
Nader L.
Stanford University, USA
Total Synthesis of (±)-Panacene.
J. Am. Chem. Soc. 1982;
104: 4011-4012
Key words
(±)-panacene - marine natural products - bromoallene - Williamson ether synthesis - Dieckmann condensation - bromoetherification
Significance
The marine natural product panacene was first isolated in 1977 from Aplysia brasiliana and possesses antifeedant properties. In 1982, Feldman and co-workers reported the first total synthesis, establishing the relative configuration of the bromoallene.
Comment
Benzofuran D was accessed by means of Dieckmann condensation and further transformed to alcohol I. Treatment with NBS led to cyclization affording bromide J which was elaborated to aldehyde L. Subjecting propargylic mesylate O to LiCuBr2 furnished the natural product.
