Journal
TETRAHEDRON
Volume 71, Issue 35, Pages 5835-5848Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.05.050
Keywords
Macrolactone; Macrocyclization; Liebeskind coupling; Triene; Total synthesis
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Funding
- Les Laboratoires Servier
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A diastereomer of wortmannilactone C was synthesized according to a versatile strategy from tert-butyl 3-hydroxypropanoate and ethyl (R)-3-hydroxybutanoate, by using versatile organometallic reagents to control four stereogenic centers out of five. The successful strategy consists of the construction of the C13-C17 triene by using a Liebeskind coupling and the construction of the C2-C7 triene by utilizing a Horner-Wadsworth-Emmons reaction to form the macrocycle. (C) 2015 Elsevier Ltd. All rights reserved.
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