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Literature DB >> 18067313

A total synthesis of OSW-1.

Jie Xue¹, Peng Liu, Yanbin Pan, Zhongwu Guo.

Abstract

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.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 18067313 PMCID： PMC3180821 DOI： 10.1021/jo7018812

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

19 in total

1. First Total Synthesis of an Exceptionally Potent Antitumor Saponin, OSW-1.

Authors: Shaojiang Deng; Biao Yu; Yun Lou; Yongzheng Hui
Journal: J Org Chem Date: 1999-01-08 Impact factor: 4.354

2. Synthesis of OSW-1 analogs with modified side chains and their antitumor activities.

Authors: Lehua Deng; Hao Wu; Biao Yu; Manrong Jiang; Jiarui Wu
Journal: Bioorg Med Chem Lett Date: 2004-06-07 Impact factor: 2.823

3. OSW saponins: facile synthesis toward a new type of structures with potent antitumor activities.

Authors: Bingfeng Shi; Pingping Tang; Xiaoyi Hu; Jun O Liu; Biao Yu
Journal: J Org Chem Date: 2005-12-09 Impact factor: 4.354

4. OSW-1 analogues: modification of the carbohydrate moiety.

Authors: Theophile Tschamber; Solange Adam; Yuji Matsuya; Seiji Masuda; Noriko Ohsawa; Sakiko Maruyama; Keiichi Kamoshita; Hideo Nemoto; Jacques Eustache
Journal: Bioorg Med Chem Lett Date: 2007-07-13 Impact factor: 2.823

5. A new synthesis of cholesterol and related C27 steroids.

Authors: N K Chaudhuri; R Nickolson; J G Williams; M Gut
Journal: J Org Chem Date: 1969-12 Impact factor: 4.354

6. On the relationship of OSW-1 to the cephalostatins.

Authors: C Guo; T G LaCour; P L Fuchs
Journal: Bioorg Med Chem Lett Date: 1999-02-08 Impact factor: 2.823

7. OSW-1: a natural compound with potent anticancer activity and a novel mechanism of action.

Authors: Yan Zhou; Celia Garcia-Prieto; Dennis A Carney; Rui-hua Xu; Helene Pelicano; Ying Kang; Wensheng Yu; Changgang Lou; Seiji Kondo; Jinsong Liu; David M Harris; Zeev Estrov; Michael J Keating; Zhendong Jin; Peng Huang
Journal: J Natl Cancer Inst Date: 2005-12-07 Impact factor: 13.506

A total synthesis of OSW-1.

1. First Total Synthesis of an Exceptionally Potent Antitumor Saponin, OSW-1.

2. Synthesis of OSW-1 analogs with modified side chains and their antitumor activities.

3. OSW saponins: facile synthesis toward a new type of structures with potent antitumor activities.

4. OSW-1 analogues: modification of the carbohydrate moiety.

5. A new synthesis of cholesterol and related C27 steroids.

6. On the relationship of OSW-1 to the cephalostatins.

7. OSW-1: a natural compound with potent anticancer activity and a novel mechanism of action.

8. Synthesis of OSW-1 analogues and a dimer and their antitumor activities.

Review 9. Biological activities and syntheses of steroidal saponins: the shark-repelling pavoninins.

10. Synthesis of a cholestane glycoside OSW-1 with potent cytostatic activity.

Review 1. Preferential killing of cancer cells with mitochondrial dysfunction by natural compounds.

2. Synthesis of biotinylated OSW-1.