A Total Synthesis of OSW-1

A new and practical method was developed to synthesize OSW-1, a natural saponin with potent antitumor activities, from (+)-dehydroisoandrosterone, l-arabinose, and d-xylose on gram scale. The synthesis was achieved in 10 linear steps with an overall yield of 6.4% starting from (+)-dehydroisoandroste...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-01, Vol.73 (1), p.157-161
Main Authors: Xue, Jie, Liu, Peng, Pan, Yanbin, Guo, Zhongwu
Format: Article
Language:English
Subjects:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Antineoplastic Agents, Phytogenic - chemical synthesis
Antineoplastic Agents, Phytogenic - chemistry
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Cholestenones - chemical synthesis
Cholestenones - chemistry
Exact sciences and technology
Molecular Conformation
Organic chemistry
Ornithogalum
Preparations and properties
Saponins - chemical synthesis
Saponins - chemistry
Stereoisomerism
Steroids
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Summary:A new and practical method was developed to synthesize OSW-1, a natural saponin with potent antitumor activities, from (+)-dehydroisoandrosterone, l-arabinose, and d-xylose on gram scale. The synthesis was achieved in 10 linear steps with an overall yield of 6.4% starting from (+)-dehydroisoandrosterone.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo7018812