Article

Total synthesis of (-)-5,6-dihydrocineromycin B.

Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
The Journal of Organic Chemistry (impact factor: 4.45). 01/2009; 74(3):1356-9. DOI:10.1021/jo802503x pp.1356-9
Source: PubMed

ABSTRACT An asymmetric total synthesis of (-)-5,6-dihydrocineromycin B has been accomplished in 13 steps from (-)-linalool O-triethylsilyl ether or 12 steps from geraniol. The present synthesis features (i) an intermolecular Wittig reaction involving an aldehyde possessing a ketophosphonate functionality and (ii) an intramolecular Horner-Wadsworth-Emmons olefination.

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    Article: Recent Applications of the Horner-Wadsworth-Emmons Reaction to the Synthesis of Natural Products
    Juan A. Bisceglia, Liliana R. Orelli
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    ABSTRACT: The Horner-Wadsworth-Emmons reaction has evolved in the last years as one of the most powerful and reliable method for stereocontrolled olefin synthesis. The reaction has become a widespread standard tool in natural products total syntheses, providing access to relatively simple as well as highly complex synthetic targets. In this work we present the most representative applications within the field of natural product synthesis from 2000 to the present year. The examples comprise the synthesis of macrocycles, 5 to 7 membered rings, lipids and related compounds, alkaloids and cyclic ethers. They were chosen from a large amount of literature reports and illustrate the use of the HWE reaction in the synthesis and elaboration of key intermediates and in the crucial assembly of highly functionalized synthetic precursors
    Current Organic Chemistry 11/2012; 16(19):2206. · 3.06 Impact Factor
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Keywords

-)-linalool O-triethylsilyl ether
 
intermolecular Wittig reaction
 
ketophosphonate functionality
 
present synthesis features