Journal
TETRAHEDRON
Volume 74, Issue 51, Pages 7277-7281Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.10.066
Keywords
Stille reaction.; Oxidation; Allylation; Stereoselectivity; Catalysis
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Funding
- Texas Tech University
- Plains Bridges to the Baccalaureate Program [NIH 5R25GM83730-2]
- National Science Foundation CRIF Program [CHE-1048553]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R25GM083730] Funding Source: NIH RePORTER
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Transition metal catalysis has enabled the highly stereoselective and protecting group-free synthesis of the C14-C23 fragment of the apoptosis-inducing natural products biselyngbyolide A and B. A Pd-catalyzed Stille reaction between a vinyl stannane and a crotyl carbonate formed the skipped diene with complete control of the trisubstituted bond and excellent control over the branched/linear products. A Cu-catalyzed Stahl oxidation was used to form the requisite aldehyde needed for a Ag-catalyzed asymmetric allylation. The latter provided the final fragment with excellent stereochemical control. (C) 2018 Elsevier Ltd. All rights reserved.
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