Beilstein Journal of Organic Chemistry (Oct 2014)

Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation

  • Yiyang Liu,
  • Marc Liniger,
  • Ryan M. McFadden,
  • Jenny L. Roizen,
  • Jacquie Malette,
  • Corey M. Reeves,
  • Douglas C. Behenna,
  • Masaki Seto,
  • Jimin Kim,
  • Justin T. Mohr,
  • Scott C. Virgil,
  • Brian M. Stoltz

DOI
https://doi.org/10.3762/bjoc.10.261
Journal volume & issue
Vol. 10, no. 1
pp. 2501 – 2512

Abstract

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Pd-catalyzed enantioselective alkylation in conjunction with further synthetic elaboration enables the formal total syntheses of a number of “classic” natural product target molecules. This publication highlights recent methods for setting quaternary and tetrasubstituted tertiary carbon stereocenters to address the synthetic hurdles encountered over many decades across multiple compound classes spanning carbohydrate derivatives, terpenes, and alkaloids. These enantioselective methods will impact both academic and industrial settings, where the synthesis of stereogenic quaternary carbons is a continuing challenge.

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