4.4 Article

Microwave-enhanced, stereospecific ring-closure of medium-ring cyanamide ethers to yohimbine

Journal

TETRAHEDRON LETTERS
Volume 60, Issue 17, Pages 1182-1185

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2019.03.058

Keywords

Cyanamide; Microwave irradiation; Stereospecificity; Indole chemistry

Funding

  1. University of Florida

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A highly efficient acid-promoted, stereospecific, transannular ring-closure of medium-ring ether compounds to the indole alkaloid yohimbine is described. Microwave-enhanced acetic acid degradation of cyanamide compounds involves loss of (R)- or (S)-ethers, followed by a stereospecific, nucleophilic ring-closure from the cyanamide to afford yohimbine in up to 74% yield in as little as one minute. This nucleophilic reactivity of the amino moiety of the cyanamide highlights an alternative reactivity profile from its traditional electrophilic properties. Additionally, this reaction pathway highlights a rare case of an S(N)1 pathway that proceeds with complete stereospecificity. (C) 2019 Elsevier Ltd. All rights reserved.

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