AI Article Synopsis

  • The research presents the successful stereoselective total synthesis of dechlorotrichotoxin A from the natural monoterpenoid (-)-citronellal, as well as a synthesis of a trichotoxin A mixture.! -
  • Key synthetic steps included the introduction of three alkenes and the formation of a stereogenic secondary alcohol, utilizing techniques like olefin cross-metathesis, Tebbe olefination, and enantioselective allylation with chiral phosphoric acid.! -
  • The synthesized dechlorotrichotoxin A's spectroscopic data was compared to existing reports, confirming that the isolated polyketide pertains to trichotoxin A, not dechlorotrich

Article Abstract

The stereoselective total synthesis of dechlorotrichotoxin A, alongside the synthesis of a 1:1 10/ mixture of trichotoxin A, was successfully achieved, commencing from the natural monoterpenoid (-)-citronellal. Key steps in the synthesis involved introducing three alkenes and establishing a stereogenic secondary alcohol center. These transformations were accomplished through olefin cross-metathesis, Tebbe olefination, and enantioselective allylation using a chiral phosphoric acid. A comparison of the spectroscopic data between the synthetic dechlorotrichotoxin A and the reported spectra confirmed that the polyketide isolated from a species corresponds to trichotoxin A rather than dechlorotrichotoxin A.

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Source
http://dx.doi.org/10.1021/acs.jnatprod.3c00629DOI Listing

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