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Enantioselective total synthesis of borrelidin. | LitMetric

Enantioselective total synthesis of borrelidin.

J Am Chem Soc

Department of Chemistry, Venable and Kenan Laboratories, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.

Published: February 2003

AI Article Synopsis

  • The synthesis of the natural product borrelidin was successfully completed for the first time.
  • Key methods used included catalytic enantioselective reductive aldol reactions, a catalytic Negishi coupling, and a catalytic directed hydrogenation for the propionate fragment.
  • The final steps involved fusing the propionate and vinyl iodide fragments through a catalytic Sonogashira coupling, followed by hydrostannylation and cyanation to achieve the target borrelidin structure.

Article Abstract

The first total synthesis of the natural product borrelidin is described. The propionate fragment of the molecule was concisely synthesized through catalytic enantioselective reductive aldol reactions, a catalytic Negishi coupling, and a catalytic directed hydrogenation. The propionate segment was then fused to the vinyl iodide fragment through a catalytic Sonogashira coupling. Subsequent catalytic hydrostannylation and catalytic cyanation allowed access to the target structure.

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Source
http://dx.doi.org/10.1021/ja028941uDOI Listing

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