Asymmetric synthesis of (-)-swainsonine

Yong-Shou Tian; Jae-Eun Joo; Bae-Soo Kong; Van-Thoai Pham; Kee-Young Lee; Won-Hun Ham

doi:10.1021/jo802800d

Asymmetric synthesis of (-)-swainsonine

J Org Chem. 2009 May 15;74(10):3962-5. doi: 10.1021/jo802800d.

Authors

Yong-Shou Tian¹, Jae-Eun Joo, Bae-Soo Kong, Van-Thoai Pham, Kee-Young Lee, Won-Hun Ham

Affiliation

¹ College of Pharmacy, Sung Kyun Kwan University, Suwon 440-746, Korea.

PMID: 19361186
DOI: 10.1021/jo802800d

Abstract

We report a new asymmetric synthetic method for (-)-swainsonine utilizing a chiral oxazoline precursor. The key features in this strategy are the diastereoselective oxazoline formation reaction catalyzed by palladium(0), diasteroselective dihydroxylation, and the stereocontrolled allylation reaction with TiCl(4).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents, Phytogenic / chemical synthesis
Antineoplastic Agents, Phytogenic / chemistry
Oxazoles / chemistry
Stereoisomerism
Substrate Specificity
Swainsonine / chemical synthesis*
Swainsonine / chemistry

Substances

Antineoplastic Agents, Phytogenic
Oxazoles
Swainsonine