Literature DB >> 12047177

Total synthesis of the anticancer natural product OSW-1.

Wensheng Yu1, Zhendong Jin.   

Abstract

The highly potent anticancer natural saponin OSW-1 has been successfully synthesized from commercially available 5-androsten-3beta-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 alpha-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 alpha-halo vinyl ether chemistry developed in our laboratories.

Entities:  

Mesh：

Substances：

Year:  2002        PMID： 12047177     DOI： 10.1021/ja012119t

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  8 in total

1.  A total synthesis of OSW-1.

Authors:  Jie Xue; Peng Liu; Yanbin Pan; Zhongwu Guo
Journal:  J Org Chem       Date:  2007-12-08       Impact factor: 4.354

2.  The cephalostatins. 21. Synthesis of bis-steroidal pyrazine rhamnosides (1).

Authors:  George R Pettit; Ricardo F Mendonça; John C Knight; Robin K Pettit
Journal:  J Nat Prod       Date:  2011-09-07       Impact factor: 4.050

3.  Effective killing of leukemia cells by the natural product OSW-1 through disruption of cellular calcium homeostasis.

Authors:  Celia Garcia-Prieto; Kausar Begam Riaz Ahmed; Zhao Chen; Yan Zhou; Naima Hammoudi; Ying Kang; Changgang Lou; Yan Mei; Zhendong Jin; Peng Huang
Journal:  J Biol Chem       Date:  2012-12-17       Impact factor: 5.157

4.  In Pursuit of an Ideal C-C Bond-Forming Reaction: Development and Applications of the Hydrovinylation of Olefins.

Authors:  T V Rajanbabu
Journal:  Synlett       Date:  2009       Impact factor: 2.454

5.  Ligand tuning in asymmetric hydrovinylation of 1,3-dienes: a stereoselective route to either steroid-C20 (S) or -C20 (R) derivatives.

Authors:  Biswajit Saha; Craig R Smith; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2008-06-21       Impact factor: 15.419

6.  Facile synthesis of saponins containing 2,3-branched oligosaccharides by using partially protected glycosyl donors.

Authors:  Guofeng Gu; Yuguo Du; Robert J Linhardt
Journal:  J Org Chem       Date:  2004-08-06       Impact factor: 4.354

7.  Synthesis of biotinylated OSW-1.

Authors:  Ying Kang; Changgang Lou; Kausar Begam Riaz Ahmed; Peng Huang; Zhendong Jin
Journal:  Bioorg Med Chem Lett       Date:  2009-07-14       Impact factor: 2.823

8.  Broadly Applicable Stereoselective Syntheses of Serrulatane, Amphilectane Diterpenes, and Their Diastereoisomeric Congeners Using Asymmetric Hydrovinylation for Absolute Stereochemical Control.

Authors:  Srinivasarao Tenneti; Souvagya Biswas; Glen Adam Cox; Daniel J Mans; Hwan Jung Lim; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2018-07-27       Impact factor: 15.419
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.