Enantioselective synthesis of a putative hexaketide intermediate in the biosynthesis of the squalestatins
TJ Simpson, RW Smith, SM Westaway, CL Willis…
Index: 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. Tetrahedron Letters, 1997 , vol. 38, # 30 p. 5367 - 5370
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Citation Number: 17
Abstract
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 ...
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