4.4 Article

Enantiospecific total synthesis of indole alkaloids (+)-eburnamonine, (-)-aspidospermidine and (-)-quebrachamine

Journal

TETRAHEDRON
Volume 69, Issue 26, Pages 5525-5536

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.04.097

Keywords

Indole alkaloids; Total synthesis; Enantiospecific synthesis; Claisen rearrangement

Funding

  1. Department of Science and Technology (DST), New Delhi
  2. Council of Scientific and Industrial Research (CSIR), New Delhi

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An enantiospecific total synthesis of indole alkaloids eburnamonine, aspidospermidine and quebrachamine is described from lactic acid. Synthesis of all three alkaloids is accomplished from a single chiral building block. Johnson-Claisen rearrangement of a chiral allyl alcohol is the main feature for the installation of the required quaternary centre. (C) 2013 Elsevier Ltd. All rights reserved.

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