Aldol condensation: A stereoselective approach to tetrahydrophenanthrene derivatives and 3-oxa-bicyclo[3.3.1]nonan-6-ones

Article abstract of DOI:10.1080/00397919108020787

Aldol condensation of the lithium enolate of 2 with m-methoxyphenylacetaldehyde afforded 3a and 3b with good erythro stereoselectivity (5:95). Acid catalyzed cyclization of 3a gave the tetrahydrophenanthrene 5 while 3b yielded the 3-oxobicyclononanones 6. A mechanism is discussed to account for the derived products and a detailed ¹H NMR structural analysis of the [3.3.1] bicyclic systems is utilized to indirectly characterize the threo and the erythro alcohols 3a and 3b.

Full text of DOI:10.1080/00397919108020787

This article was downloaded by: [Michigan State University]
On: 27 February 2015, At: 09:26
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
Aldol Condensation: A
Stereoselective Approach
to Tetrahydrophenanthrene
Derivatives and 3-Oxa-
bicyclo[3.3.1]nonan-6-ones
Phillip A. Zoretic a , Michael S. Biggers a b
,
Christopher K. Biggers a & Myron L. Caspar a
a Department of Chemistry , East Carolina University
Greenville , North Carolina, 27858
b Central Research, Pfizer Inc. , Groton, Conn,
06340
Published online: 24 Sep 2006.
To cite this article: Phillip A. Zoretic , Michael S. Biggers , Christopher K. Biggers
& Myron L. Caspar (1991) Aldol Condensation: A Stereoselective Approach to
Tetrahydrophenanthrene Derivatives and 3-Oxa-bicyclo[3.3.1]nonan-6-ones, Synthetic
Communications: An International Journal for Rapid Communication of Synthetic
Organic Chemistry, 21:1, 31-42, DOI: 10.1080/00397919108020787
To link to this article: http://dx.doi.org/10.1080/00397919108020787
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