4.4 Article

Stereoselective synthesis of the C14-C23 fragment of biselyngbyolide A and B enabled by transition metal catalysis

Journal

TETRAHEDRON
Volume 74, Issue 51, Pages 7277-7281

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.10.066

Keywords

Stille reaction.; Oxidation; Allylation; Stereoselectivity; Catalysis

Funding

  1. Texas Tech University
  2. Plains Bridges to the Baccalaureate Program [NIH 5R25GM83730-2]
  3. National Science Foundation CRIF Program [CHE-1048553]
  4. 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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