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Synthesis 2015; 47(14): 2129-2137
DOI: 10.1055/s-0034-1380780
DOI: 10.1055/s-0034-1380780
paper
Total Synthesis of the Nonenolide Xyolide Using a Regioselective Nucleophilic Epoxide Opening Approach
Further Information
Publication History
Received: 10 November 2014
Accepted after revision: 20 April 2015
Publication Date:
19 June 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201514/lookinside/thumbnails/ss-2014-n0687-op_10-1055_s-0034-1380780-1.jpg)
Abstract
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.
Key words
natural product - xyolide - Sharpless epoxidation - regioselective ring opening - ring-closing metathesisSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380780.
- Supporting Information
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