4.0 Article

Stereocontrolled total synthesis of (-)-myriocin

Journal

TETRAHEDRON-ASYMMETRY
Volume 19, Issue 24, Pages 2771-2773

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2008.12.020

Keywords

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Funding

  1. Takeda Science Foundation
  2. Naito Foundation
  3. Nagase Science and Technology Foundation
  4. Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan [12045232]
  5. Grants-in-Aid for Scientific Research [12045232] Funding Source: KAKEN

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The stereocontrolled total synthesis of (-)-myriocin 1 is reported. Optically active epoxide 9 was converted from symmetrical cyclohexadiene 8, utilizing an enzymatic kinetic resolution. The three sequential stereogenic centers of 1 were constructed by a regioselective epoxide-opening reaction and a Hofmann rearrangement. Elongation of the side chain was efficiently accomplished by the Julia-Kocienski reaction. Published by Elsevier Ltd.

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