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Stereoselective synthesis of radiolabelled avermectins

✍ Scribed by Bruce P. McKillican; Jeffrey W. Perine; Dana P. Simmons; Timothy E. Wilson

Publisher
John Wiley and Sons
Year
2005
Tongue
French
Weight
116 KB
Volume
48
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The natural products avemectin B~1a~ 1a and B~1b~ 1b were each site‐specifically ^14^C labelled at carbon 23 in a convergent synthesis for metabolism, residue, and environmental studies. The 12‐step radiosynthesis involved a stereoselective aldol condensation and later a coupling to a protected avermectin degradate 2 in a one‐pot Wittig condensation/spiroketalization to reconstitute the dioxaspirane configuration found in the natural products. Copyright © 2004 John Wiley & Sons, Ltd.

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