Journal
TETRAHEDRON LETTERS
Volume 49, Issue 44, Pages 6341-6343Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.08.065
Keywords
Asymmetric synthesis; Eleutherins; Nocardiones; Dotz annotation; Oxa-Pictet Spengler reaction
Categories
Funding
- IRCC
- Department of Chemistry, IIT-Bombay
- INSA, New Delhi
- CSIR, New Delhi
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A short enantioselective synthesis of (+)-eleutherin, (+)-allo-eleutherin and the formal synthesis of (+)-nocardione B is described. The synthesis is completed in six steps in overall yields of 8% for eleutherin and 14% for allo-eleutherin. The synthetic strategy features ail efficient combination of the Dotz annulation reaction with a chiral alkyne and an oxa-Pictet Spengler reaction as the keys steps in the stereodivergent synthesis of (+)-eleutherin and (+)-allo-eleutherin. The synthesis of (S)-(+)-2-(2'-hydroxypropyl)-5-methoxy-1,4-naphthoquinone entails the formal synthesis of (+)-nocardione B. (c) 2008 Elsevier Ltd. All rights reserved.
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