Journal
TETRAHEDRON LETTERS
Volume 51, Issue 38, Pages 5091-5093Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.07.119
Keywords
Bistramide; Tetrahydropyrans; Intramolecular oxa-Michael addition; Cyclization
Categories
Funding
- European Community (European Union) [LSHB-CT-2004-503467]
- CNRS
- University Lyon 1
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The C1-C13 fragment of bistramide A was prepared from 5-hexenoic acid in 15 linear steps and in 16% overall yield. The core 2,6-trans-tetrahydropyran ring was obtained via a kinetically controlled oxa-Michael cyclization from the corresponding chiral alpha,beta-unsaturated hydroxyester. This precursor was prepared by using a diastereoselective alkylation reaction using Davies Superquat auxiliary and a diastereoselective Roush's allylboration as key steps. (C) 2010 Elsevier Ltd. All rights reserved.
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