Asymmetric Synthesis of (−)-Swainsonine

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

doi:10.1021/jo802800d.s002

jo802800d_si_002.pdf (3.82 MB)

Asymmetric Synthesis of (−)-Swainsonine

journal contribution

posted on 2009-05-15, 00:00 authored by Yong-Shou Tian, Jae-Eun Joo, Bae-Soo Kong, Van-Thoai Pham, Kee-Young Lee, Won-Hun Ham

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 TiCl₄.