Issue 91, 2012
From the journal:

Chemical Communications

An expedient approach to the total synthesis of (+)-5-epi-eudesm-4(15)-ene-1β,6β-diol†

Gowrisankar Parthasarathy,a   Céline Besnardb  and  E. Peter Kündig*a  

* Corresponding authors

a Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, 1211 Geneva 4, Switzerland
E-mail: peter.kundig@unige.ch
Web: http://www.unige.ch/sciences/chiorg/kundig/
Fax: +41 22-379-3215
Tel: +41 22-379-6093

b Laboratoire de Cristallographie, University of Geneva, 24 Quai Ernest Ansermet, 1211 Geneva 4, Switzerland

Abstract

The first total synthesis of (+)-5-epi-eudesm-4(15)-ene-1β,6β-diol has been achieved in 12 steps starting from the known (−)-cis-piperitol and by using a chelation controlled glycolate enolate Ireland–Claisen rearrangement and an intramolecular nitrile oxide dipolar cycloaddition as key steps.

Graphical abstract: An expedient approach to the total synthesis of (+)-5-epi-eudesm-4(15)-ene-1β,6β-diol

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Article information

DOI
https://doi.org/10.1039/C2CC36260K
Article type
Communication
Submitted
28 Aug 2012
Accepted
25 Sep 2012
First published
26 Sep 2012

Chem. Commun., 2012,48, 11241-11243

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An expedient approach to the total synthesis of (+)-5-epi-eudesm-4(15)-ene-1β,6β-diol

G. Parthasarathy, C. Besnard and E. P. Kündig, Chem. Commun., 2012, 48, 11241 DOI: 10.1039/C2CC36260K

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