Citation: Xiao-Gang Wang, Ai-E Wang, Pei-Qiang Huang. A concise formal stereoselective total synthesis of (—)-swainsonine[J]. Chinese Chemical Letters, ;2014, 25(2): 193-196. shu

A concise formal stereoselective total synthesis of (—)-swainsonine

1.
a Department of Chemistry, College of Chemistry and Chemical Engineering, and Fujian Provincial Key Laboratory of Chemical Biology, Xiamen University,Xiamen 361005, China;
2.
b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China

Corresponding author: Pei-Qiang Huang,
Received Date: 28 August 2013
Available Online: 8 November 2013

A short formal stereoselective synthesis of (—)-swainsonine (1) is described. Our synthesis started with the versatile building block (R)-3-benzyloxyglutarimide 5. Through controlled regioselective reduction, Ley's-sulfone chemistry (N-α-sulfonylation and ZnCl₂-catalyzed N-α-amidovinylation), an RCM reaction, and an amide reduction, the synthesis of unsaturated indolizidine (8R,8aS)-3 has been achieved in five steps. The indolizidine (8R,8aS)-3 is an advanced intermediate toward the synthesis of (—)-swainsonine (1).
- Indolizidines,
- Alkaloids,
- α-Amidoalkylation,
- Building blocks,
- Stereoselective synthesis
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