Convergent and stereoselective synthesis of (−)-zeaenol

Stereoselective synthesis of (−)-zeaenol has been accomplished from d-xylose as a chiral pool starting material. The key steps of this convergent synthetic strategy involves a Stille coupling, a Noyori reduction, a Julia–Kocienski olefination and a macrolactonization to obtain (−)-zeaenol. We have a...

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Bibliographic Details
Published in:Tetrahedron 2015-08, Vol.71 (34), p.5669-5677
Main Authors: Kumar, Rayala Naveen, Meshram, H.M.
Format: Article
Language:English
Subjects:
d-xylose
Intramolecular hydrosilylation
Julia–Kocienski olefination
Sonogashira coupling
Stille coupling
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Summary:Stereoselective synthesis of (−)-zeaenol has been accomplished from d-xylose as a chiral pool starting material. The key steps of this convergent synthetic strategy involves a Stille coupling, a Noyori reduction, a Julia–Kocienski olefination and a macrolactonization to obtain (−)-zeaenol. We have also explored a Sonogashira coupling along with a Trost protocol for the intramolecular hydrosilylation on the homopropargylic alcohol system as an alternative synthetic approach to this molecule. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.06.035