Total Synthesis of the Nonenolide Xyolide Using a Regioselective Nucleophilic Epoxide Opening Approach

The total synthesis of the nonenolide xyolide is described as a convergent synthesis in 16 steps from the commercially available starting material butane-1,4-diol. The key reactions involved are: Sharpless asymmetric epoxidation, Pinnick oxidation, acid-mediated nucleophilic regioselective epoxide r...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 47; no. 14; pp. 2129 - 2137
Main Authors Wadavrao, Sachin B., Ghogare, Ramesh S., Narsaiah, A. Venkat
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 17.07.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIDATION
FUNGUS
natural product
Sharpless epoxidation
EFFICIENT SYNTHESIS
READY ACCESS
regioselective ring opening
STEREOSELECTIVE TOTAL-SYNTHESIS
CHIRAL EPOXYALLYL ALCOHOLS
ring-closing metathesis
HYDRIDE
AGENT
ACHAETOLIDE
xyolide
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Summary:The total synthesis of the nonenolide xyolide is described as a convergent synthesis in 16 steps from the commercially available starting material butane-1,4-diol. The key reactions involved are: Sharpless asymmetric epoxidation, Pinnick oxidation, acid-mediated nucleophilic regioselective epoxide ring opening, Steglich esterification, and ring-closing metathesis.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1380780