Chiral vicinal diols as platforms for separable diastereomers in Johnson–Claisen rearrangement: a new short route to (−)-nor-canadensolide, (−)-canadensolide and (−)-sporothriolide

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 γ-(lactone-lactol) intermediates (in six steps...

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Bibliographic Details
Published in:Tetrahedron letters 2009-03, Vol.50 (10), p.1122-1124
Main Authors: Fernandes, Rodney A., Ingle, Arun B.
Format: Article
Language:English
Subjects:
Asymmetric synthesis
Canadensolide
Chiral vicinal diols
Johnson–Claisen rearrangement
Nor-canadensolide
Sporothriolide
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Summary: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 γ-(lactone-lactol) intermediates (in six steps, 26–27% overall yields) for the synthesis of (−)-nor-canadensolide, (−)-canadensolide and (−)-sporothriolide.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.12.084