Download PDF
Synfacts 2021; 17(08): 0854
DOI: 10.1055/s-0040-1719666
Synthesis of Natural Products and Potential Drugs

Synthesis of (±)-Panacene

Contributor(s):
Erick M. Carreira
,
Fabian Glatz
Feldman KS, *, Mechem CC, Nader L. Stanford University, USA
Total Synthesis of (±)-Panacene.

J. Am. Chem. Soc. 1982;
104: 4011-4012
CrossrefSearch in Google Scholar
› Further Information
 
 PDF Download Permissions and Reprints

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.


#
#

Publication History

Article published online:
20 July 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany


   Permissions and Reprints