4.4 Article

Synthesis of (±)-lecanindole D

Journal

TETRAHEDRON LETTERS
Volume 54, Issue 34, Pages 4561-4563

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.06.084

Keywords

Lecanindole; Indole sesquiterpene; Progesterone receptor agonist; Alkaloid

Funding

  1. Ministry of Education, Culture, Sports, Science and Technology of Japan [23780112]
  2. Grants-in-Aid for Scientific Research [23780112] Funding Source: KAKEN

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The first synthesis of the racemate of lecanindole D, an indole sesquiterpenoid with potent and selective agonist activity toward the progesterone receptor, has been achieved from a known tetracyclic alcohol by using a diastereoselective installation of its tertiary hydroxy group via an epoxide intermediate and a Pd(II)-mediated construction of the indole ring moiety as the key transformations. (C) 2013 Elsevier Ltd. All rights reserved.

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