Journal article
Total Synthesis of the Anticancer Natural Product OSW-1
Journal of the American Chemical Society, Vol.124(23), pp.6576-6583
06/12/2002
DOI: 10.1021/ja012119t
PMID: 12047177
Abstract
The highly potent anticancer natural saponin OSW-1 has been successfully synthesized from commercially available 5-androsten-3β-ol-17-one 79 in 10 operations with 28% overall yield. The key steps in the total synthesis included a highly regio- and stereoselective selenium dioxide-mediated allylic oxidation of 80 and a highly stereoselective 1,4-addition of α-alkoxy vinyl cuprates 68 to steroid 17(20)-en-16-one 12E to introduce the steroid side chain. This total synthesis demonstrated once again the versatile synthetic applications of α-halo vinyl ether chemistry developed in our laboratories.
Details
- Title: Subtitle
- Total Synthesis of the Anticancer Natural Product OSW-1
- Creators
- Wensheng YU - University of IowaZhendong Jin - University of Iowa
- Resource Type
- Journal article
- Publication Details
- Journal of the American Chemical Society, Vol.124(23), pp.6576-6583
- Publisher
- American Chemical Society
- DOI
- 10.1021/ja012119t
- PMID
- 12047177
- ISSN
- 0002-7863
- eISSN
- 1520-5126
- Language
- English
- Date published
- 06/12/2002
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Medicinal and Natural Products Chemistry
- Record Identifier
- 9984366025002771
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