Issue 10, 2017

Gold(i)-catalyzed access to neomerane skeletons

Abstract

The gold(I) catalyzed cycloisomerization of an enynyl propargylic ester, featuring a 1,2-acyloxy migration/intramolecular cyclopropanation sequence, opens a straightforward access to the 5,7,3-tricyclic skeleton of neomerane sesquiterpenes. The first total synthesis of 5-epi-valeneomerin B in 12 steps with an overall yield of 5.3% from the readily available hex-5-en-2-one is reported.

Graphical abstract: Gold(i)-catalyzed access to neomerane skeletons

Supplementary files

Article information

Article type
Research Article
Submitted
07 میٔ 2017
Accepted
10 جوٗن 2017
First published
12 جوٗن 2017

Org. Chem. Front., 2017,4, 1906-1916

Gold(I)-catalyzed access to neomerane skeletons

C. Tugny, O. Khaled, E. Derat, J. Goddard, V. Mouriès-Mansuy and L. Fensterbank, Org. Chem. Front., 2017, 4, 1906 DOI: 10.1039/C7QO00360A

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