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A short enantioselective synthesis of (+)-eleutherin, (+)-allo-eleutherin and a formal synthesis of (+)-nocardione B

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Title A short enantioselective synthesis of (+)-eleutherin, (+)-allo-eleutherin and a formal synthesis of (+)-nocardione B
 
Creator FERNANDES, RA
CHAVAN, VP
INGLE, AB
 
Subject tyrosine phosphatase inhibitors
naturally-occurring quinones
pyranonaphthoquinone antibiotics
radical cyclization
efficient synthesis
dimethyl ether
nocardione-a
frenolicin-b
nanaomycin-a
(&/-)-nanaomycin-a
asymmetric synthesis
eleutherins
nocardiones
dotz annotation
oxa-pictet spengler reaction
 
Description 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
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2011-08-23T09:19:30Z
2011-12-26T12:56:23Z
2011-12-27T05:45:05Z
2011-08-23T09:19:30Z
2011-12-26T12:56:23Z
2011-12-27T05:45:05Z
2008
 
Type Article
 
Identifier TETRAHEDRON LETTERS, 49(44), 6341-6343
0040-4039
http://dx.doi.org/10.1016/j.tetlet.2008.08.065
http://dspace.library.iitb.ac.in/xmlui/handle/10054/10471
http://hdl.handle.net/10054/10471
 
Language en