Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/xmlui/handle/10054/10616
Title: Chiral vicinal diols as platforms for separable diastereomers in Johnson-Claisen rearrangement: a new short route to (-)-nor-canadensolide, (-)-canadensolide and (-)-sporothriolide
Authors: FERNANDES, RA
INGLE, AB
Keywords: Enantioselective Synthesis
Formal Synthesis
Asymmetric Dihydroxylation
Stereoselective Synthesis
Efficient Synthesis
Diacetone Glucose
Allylic Alcohols
Gamma-Lactones
Canadensolide
Sporothriolide
Issue Date: 2009
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Citation: TETRAHEDRON LETTERS, 50(10), 1122-1124
Abstract: The chiral vicinal diols prepared by asymmetric dihydroxylation in high enantioselectivities provide an excellent platform for separable diastereomers in the Johnson-Claisen rearrangement. The separated syn-diastereomers were converted into the advanced gamma-(lactone-lactol) intermediates (in six steps, 26-27% overall yields) for the synthesis of (-)-nor-canadensoiide, (-)-canadensolide and (-)-sporothriolide. (C) 2009
URI: http://dx.doi.org/10.1016/j.tetlet.2008.12.084
http://dspace.library.iitb.ac.in/xmlui/handle/10054/10616
http://hdl.handle.net/10054/10616
ISSN: 0040-4039
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