4.8 Article

Total Synthesis of (-)-Anisatin

Journal

ORGANIC LETTERS
Volume 14, Issue 6, Pages 1632-1635

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol300390k

Keywords

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Funding

  1. Japan Society for the Promotion of Science (JSPS) [20002004, 22590002]
  2. Research Foundation for Pharmaceutical Sciences
  3. Mochida Memorial Foundation for Medical and Pharmaceutical Research
  4. Uehara Memorial Foundation
  5. Grants-in-Aid for Scientific Research [10J01765, 20002004] Funding Source: KAKEN

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A novel synthetic route to (-)-anisatin has been developed. Our synthesis features a rhodium-catalyzed 1,4-addition of an arylboronic acid, an intramolecular Diels Alder reaction of an ortho-quinone monoketal, a stereoselective [2,3]-Wittig rearrangement, and construction of the oxabicyclo [3.3.1] skeleton via cleavage of an epoxide by a primary amide.

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