Studies towards the synthesis of the C(8)-C(15) fragment of tedanolide
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Date
2004
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Montana State University - Bozeman, College of Letters & Science
Abstract
Tedanolide is a 18-membered macrolide of marine origin which displays antitumor activity and
presents a synthetic challenge. To date, the total synthesis of tedanolide has not been reported however
the synthesis of 13-deoxytedanolide, another closely related macrolide isolated from a different sea
sponge, was recently accomplished.
Progress towards the synthesis of tedanolide is described with specific attention given to the synthesis
of the C(8)-C(15) portion of the molecule. The approach involves the use of rigid bicyclic ring systems
to control the stereocenters found in the natural product. The approach contained herein has not yet led
to the total synthesis of tedanolide but has led to a precursor of the 18-membered ring.