4.4 Article

First total synthesis and stereochemical revision of okaramine M

Journal

TETRAHEDRON LETTERS
Volume 51, Issue 46, Pages 6003-6005

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.09.026

Keywords

Diketopiperazine; Pyrrolo[2,3-b]indole; Asymmetric synthesis; Oxidation

Funding

  1. Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan [19590020, S0801043]
  2. Grants-in-Aid for Scientific Research [19590020, 21590028] Funding Source: KAKEN

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We describe the first total synthesis of the reported and revised structures of okaramine M (1 and 7) through the Ugi three-component reaction of pyrroloindole imine 10 with p-methoxyphenyl isonitrile and N-Boc-L-tryptophan, followed by cyclization and epimerization. (C) 2010 Elsevier Ltd. All rights reserved.

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