Diastereoselective addition of organomagnesium reagents to 17β-TBDMS- dihydrotestosterone

Article abstract of DOI:10.1080/00397919908086075

Several alkylations of the C3-carbonyl of 17β-TBDMS-DHT (1) with Grignard reagents were performed to obtain a series of potential inhibitors of androgen formation. It has been found that, depending on the nucleophilicity of the Grignard reagent used, there was a difference in the diastereoselectivity. The stronger reagents proceeded preferentially through the equatorial attack, while the weaker ones proceeded through the axial attack.

Full text of DOI:10.1080/00397919908086075

This article was downloaded by: [University of Auckland Library]
On: 30 November 2014, At: 12:31
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
Diastereoselective Addition
of Organomagnesium
Reagents to 17β-TBDMS-
Dihydrotestosterone
a
a
BÉAtrice Tchédam Ngatcha & Donald Poirier
a
Division of Medicinal Chemistry, Laboratory of
Molecular Endocrinology, CHUL Research Center and
Laval University , Quebec, Canada , G1V 4G2
Published online: 17 Sep 2007.
To cite this article: BÉAtrice Tchédam Ngatcha & Donald Poirier (1999)
Diastereoselective Addition of Organomagnesium Reagents to 17β-TBDMS-
Dihydrotestosterone, Synthetic Communications: An International Journal for
Rapid Communication of Synthetic Organic Chemistry, 29:7, 1065-1074, DOI:
10.1080/00397919908086075
To link to this article: http://dx.doi.org/10.1080/00397919908086075
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