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Synfacts 2021; 17(08): 0854
DOI: 10.1055/s-0040-1719666
DOI: 10.1055/s-0040-1719666
Synthesis of Natural Products and Potential Drugs
Synthesis of (±)-Panacene
Feldman KS,
*,
Mechem CC,
Nader L.
Stanford University, USA
Total Synthesis of (±)-Panacene.
J. Am. Chem. Soc. 1982;
104: 4011-4012
DOI: 10.1021/ja00378a042.
Total Synthesis of (±)-Panacene.
J. Am. Chem. Soc. 1982;
104: 4011-4012
DOI: 10.1021/ja00378a042.
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.
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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.
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Publication History
Article published online:
20 July 2021
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