4.4 Article

First enantioselective total synthesis of (S)-(-)-longianone

期刊

TETRAHEDRON
卷 68, 期 19, 页码 3725-3728

出版社

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.03.021

关键词

1,2-Cyclopropanecarboxylate; One-pot reaction; Intramolecular hetero Michael addition; 1,7-Dioxaspiro[4,4]nonane; Carbohydrates

资金

  1. Council of Scientific and Industrial Research (CSIR), New Delhi, India [01(2408)/10/EMR-II]
  2. CSIR

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An efficient stereoselective synthesis of (S)-(-)-longianone was achieved from sugar derived 1,2-cyclopropanecarboxylate involving bromonium ion mediated solvolytic ring opening and a one-pot dehydrohalogenation, stereoselective intramolecular hetero Michael addition (IHMA) and ester hydrolysis as key steps. (C) 2012 Elsevier Ltd. All rights reserved.

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