4.8 Article

Modular Terpenoid Construction via Catalytic Enantioselective Formation of All-Carbon Quaternary Centers: Total Synthesis of Oridamycin A, Triptoquinones B and C, and Isoiresin

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 38, Pages 12364-12367

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b08902

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Funding

  1. Robert A. Welch Foundation [F-0038]
  2. NIH-NIGMS [RO1-GM093905]

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Total syntheses of oridamycin A, triptoquinones B and C, and isoiresin are accomplished from a common intermediate prepared via iridium-catalyzed alcohol CH tert-(hydroxy)prenylation - a byproduct-free process that forms an all-carbon quaternary stereocenter with excellent control of diastereo- and enantioselectivity.

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