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Gold(I)-catalyzed access to neomerane skeletons

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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

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Publication details

The article was received on 07 May 2017, accepted on 10 Jun 2017 and first published on 12 Jun 2017


Article type: Research Article
DOI: 10.1039/C7QO00360A
Citation: Org. Chem. Front., 2017, Advance Article
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    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, Advance Article , DOI: 10.1039/C7QO00360A

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