4.4 Article

Facile two-step synthesis of crispine A and harmicine by cyclopropylimine rearrangement

Journal

TETRAHEDRON LETTERS
Volume 52, Issue 31, Pages 4014-4016

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.05.117

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Funding

  1. GVK Biosciences Private Limited
  2. analytical department

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The synthesis of 4 and 8 is reported. These intermediates are obtained by a one-pot tandem cyclization of 1 and 6, respectively, via Bischler Napieralski reaction followed by cyclopropylimine rearrangement. Compounds 4 and 8 were reduced by sodium borohydride in methanol to afford cytotoxic alkaloid (+/-)-crispine A and antileishmania compound (+/-)-harmicine. (C) 2011 Elsevier Ltd. All rights reserved.

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