A general synthesis of (+)-γ-substituted γ-butyrolactones using a kinetic alkylation-ozonolysis procedure

Article abstract of DOI:10.1080/00397919408011738

A synthesis of (±)-γ-substituted γ-butyrolactones is described in which the key intermediates, γ-ketoesters, are prepared from the readily available 6-methyl-5-hepten-2-one using a kinetic alkylation-ozonolysis procedure; the method allows terminal ester and Z-alkene groups to be incorporated into the side-chain and thus can be used for the synthesis of (+)-γ-jasmolactone as well as other naturally occurring lactones.

Full text of DOI:10.1080/00397919408011738

This article was downloaded by: [University of Texas Libraries]
On: 26 January 2015, At: 06:37
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 General Synthesis of (±)-γ-
Substituted γ-Butyrolactones
Using a Kinetic Alkylation-
Ozonolysis Procedure
a
a
Dermot J. Gavin & Niall W. A. Geraghty
a
Chemistry Department , University College ,
Galway, Ireland
Published online: 23 Sep 2006.
To cite this article: Dermot J. Gavin & Niall W. A. Geraghty (1994) A General
Synthesis of (±)-γ-Substituted γ-Butyrolactones Using a Kinetic Alkylation-
Ozonolysis Procedure, Synthetic Communications: An International Journal for
Rapid Communication of Synthetic Organic Chemistry, 24:10, 1351-1361, DOI:
10.1080/00397919408011738
To link to this article: http://dx.doi.org/10.1080/00397919408011738
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