4.8 Article

Total Synthesis of (-)-Isoschizogamine

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 29, Pages 11995-11997

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja305856q

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 [22590002, 20002004] Funding Source: KAKEN

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A first asymmetric total synthesis of (-)-isoschizogamine has been accomplished. Our synthesis features the facile construction of the carbon framework of the natural product through a Wagner-Meerwein rearrangement, a tandem metathesis, a stereo-selective rhodium-mediated 1,4-addition of an arylboronic acid, and a ring-closing metathesis via a hemiaminal ether.

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