Tetrahedron Letters p. 5367 - 5370 (1997)
Update date:2022-08-03
Topics:
Simpson, Thomas J.
Smith, Robert W.
Westaway, Susan M.
Willis, Christine L.
Buss, Antony D.
Cannell, Richard J. P.
Dawson, Michael J.
Rudd, Brian A. M.
A convergent synthesis of (3R, 5Z, 8E, 10R)-3-hydroxy-8,10-dimethyl-11-phenylundec-5,8-dienoic acid 4, a putative hexaketide intermediate in the biosynthesis of the squalestatins, is described. A key step in the assembly of the carbon framework is the coupling of alkyne 19 with allylic bromide 13 giving, after further functional group manipulations, the target compound as a single diastereomer. The approach may be adapted for the preparation of the corresponding (3S, 5Z, 8E, 10R)-isomer as well as for the incorporation of carbon-13 labels required for biosynthetic studies.
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Doi:10.1021/jo01257a036
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(1997)
