Total Synthesis of the Proposed Structure of Penasulfate A: l-Arabinose as a Source of Chirality

J Nat Prod. 2019 Jul 26;82(7):1908-1916. doi: 10.1021/acs.jnatprod.9b00245. Epub 2019 Jun 26.

Abstract

The total synthesis of putative penasulfate A was effectively achieved by a convergent strategy with a longest linear sequence of 14 steps and overall yield of 8.6%. The highlights of our strategy involved an E-selective olefin cross-metathesis, Suzuki cross-coupling, and a copper(I)-catalyzed coupling reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Arabinose / chemistry*
  • Catalysis
  • Fatty Acids / chemical synthesis*
  • Fatty Acids / chemistry*
  • Molecular Structure
  • Pipecolic Acids / chemical synthesis*
  • Pipecolic Acids / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Fatty Acids
  • Pipecolic Acids
  • penasulfate A
  • Arabinose