Stereospecific synthesis of steroidal 20,16-γ-carbolactones

Article abstract of DOI:10.1080/00397919808004965

Two strategies have been explored for the synthesis of steroidal 20,16- γ-carbolactones from the corresponding 17-ketoandrostane. A highly efficient, stereospecific protocol has been developed for the β-oriented cis-γ-lactone, based on a Michael addition of cyanide to a conjugated ketone. A different approach, involving prior attachment of a 3-carbon side chain on C-17 of a 17-oxo-16β-acetoxy-androstane led to the epimeric, α- oriented lactone.

Full text of DOI:10.1080/00397919808004965

This article was downloaded by: [Stanford University Libraries]
On: 24 August 2012, At: 15:38
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
Stereospecific Synthesis
of Steroidal 20,16-γ-
Carbolactones
Andrea C. Bruttomesso a , Darío Doller a b
Eduardo G Gros a
&
a Departamento de Química Orgánica, Facultad
de Ciencias Exactas y Naturales, Universidad de
Buenos Aires, Pabellón 2, Ciudad Universitaria,
1428, Buenos Aires, Argentina
b Schering-Plough Research Institute, 2015
Galloping Hill Road, Konilworth, NJ, 07033,
U.S.A.
Version of record first published: 16 Aug 2006
To cite this article: Andrea C. Bruttomesso, Darío Doller & Eduardo G Gros
(1998): Stereospecific Synthesis of Steroidal 20,16-γ-Carbolactones, Synthetic
Communications: An International Journal for Rapid Communication of Synthetic
Organic Chemistry, 28:21, 4043-4057
To link to this article: http://dx.doi.org/10.1080/00397919808004965
PLEASE SCROLL DOWN FOR ARTICLE
Full terms and conditions of use: http://www.tandfonline.com/page/
terms-and-conditions

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.
The publisher does not give any warranty express or implied or make
any representation that the contents will be complete or accurate or
up to date. The accuracy of any instructions, formulae, and drug doses
should be independently verified with primary sources. The publisher
shall not be liable for any loss, actions, claims, proceedings, demand, or
costs or damages whatsoever or howsoever caused arising directly or
indirectly in connection with or arising out of the use of this material.