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Tetrahedron Letters
Volume 39, Issue 51, 17 December 1998, Pages 9361-9364
 
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doi:10.1016/S0040-4039(98)02110-8    How to Cite or Link Using DOI (Opens New Window)
Copyright © 1998 Published by Elsevier Ltd.

A divergent approach to the myriaporones and tedanolide: Enantioselective preparation of the common intermediate

Richard E. Taylor*, a, Jeffrey P. Ciavarria and Brian R. Hearna

aDepartment of Chemistry and Biochemistry, 251 Nieuwland Science Hall University of Notre Dame, Notre Dame, IN 46556 USA

Received 25 August 1998; 
accepted 1 October 1998. 
Available online 9 February 1999.

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Abstract

The tedanolide and myriaporone classes of natural products represent interesting targets for synthesis because of their structural similarity and biological activity. The asymmetric preparation of a potential common intermediate in the total synthesis of each of these targets is presented. The key step, a Zr-mediated allylation, allows for the efficient preparation of the hydroxypropionate structural unit.

A synthetic approach to the structurally-related natural products, myriaporone 4 and tedanolide, is presented. The key step, a Zr-mediated allylation, allows for the efficient preparation of the hydroxypropionate structural unit.



Tetrahedron Letters
Volume 39, Issue 51, 17 December 1998, Pages 9361-9364
 
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