A versatile approach towards enantiopure α-methyl β-hydroxy ketones. Application to the synthesis of (4R,5S) sitophilure and of its stereoisomers

Article abstract of DOI:10.1080/00397919808004830

Rice weevil pheromone sitophilure ((4R,5S)-5-hydroxy-4-methyl-3- heptanone) and its three diastereomers were synthesized in three steps, starting from 3-(trimethylsilyloxy)-1,3-pentadiene and propionaldehyde. Other optically active α-methyl β-hydroxy ketones can also be synthesized by the reported procedure.

Full text of DOI:10.1080/00397919808004830

This article was downloaded by: [University Library Utrecht]
On: 06 August 2013, At: 05:41
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number:
1072954 Registered office: Mortimer House, 37-41 Mortimer Street,
London W1T 3JH, UK
Synthetic Communications:
An International Journal
for Rapid Communication of
Synthetic Organic Chemistry
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
A Versatile Approach
Towards Enantiopure α-
Methyl β-Hydroxy Ketones.
Application to the Synthesis
of (4R,5S) Sitophilure and of
Its Stereoisomers
Christophe Delas a , Jan Szymoniak b , Nadine
Thery a & Claude Moïse a
a Laboratoire de Synthèse et d'Electrosynthèse
Organométalliques (UMR 5632), Faculté des
Sciences, 6 bd Gabriel, 21000, Dijon, France
b Réactions Sélectives et Applications (UMR
6519), Université de Reims, 51687, Reims Cédex
2, France
Published online: 20 Aug 2006.
To cite this article: Christophe Delas , Jan Szymoniak , Nadine Thery &
Claude Mose (1998) A Versatile Approach Towards Enantiopure α-Methyl β-
Hydroxy Ketones. Application to the Synthesis of (4R,5S) Sitophilure and of
Its Stereoisomers, Synthetic Communications: An International Journal for
Rapid Communication of Synthetic Organic Chemistry, 28:14, 2613-2620, DOI:
10.1080/00397919808004830
To link to this article: http://dx.doi.org/10.1080/00397919808004830

PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all
the information (the “Content”) contained in the publications on our
platform. However, Taylor & Francis, our agents, and our licensors
make no representations or warranties whatsoever as to the accuracy,
completeness, or suitability for any purpose of the Content. Any opinions
and views expressed in this publication are the opinions and views of
the authors, and are not the views of or endorsed by Taylor & Francis.
The accuracy of the Content should not be relied upon and should be
independently verified with primary sources of information. Taylor and
Francis shall not be liable for any losses, actions, claims, proceedings,
demands, costs, expenses, damages, and other liabilities whatsoever
or howsoever caused arising directly or indirectly in connection with, in
relation to or arising out of the use of the Content.
This article may be used for research, teaching, and private study
purposes. Any substantial or systematic reproduction, redistribution,
reselling, loan, sub-licensing, systematic supply, or distribution in any
form to anyone is expressly forbidden. Terms & Conditions of access
and use can be found at http://www.tandfonline.com/page/terms-and-
conditions