Download PDF
Synlett 1995; 1995(5): 404-406
DOI: 10.1055/s-1995-5002
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Stereoselective Synthesis of (+)-Swainsonine and (-)-8,8a-Di-epi-swainsonine

Tohru Oishi, Toshihiro Iwakuma, Masahiro Hirama* , Shô Itô
  • *Department of Chemistry, Faculty of Science, Tohoku University, Sendai 980-77, Japan
Further Information

Publication History

Publication Date:
31 December 2000 (online)

 PDF Download  Permissions and Reprints All articles of this category

(+)-Swainsonine 2 and (-)-8,8a-di-epi-swainsonine 3 were stereoselectively synthesized from L-glutamic acid via a highly diastereoselective intramolecular conjugate addition of amide 20 and carbamate 8, respectively. Another key step is a stereoselective osmium-catalyzed dihydroxylation of indolizidine double bond.

(+)-swainsonine - (-)-8,8a-di-epi-swainsonine - intramolecular conjugate addition - acyloin condensation - stereocontrolled dihydroxylation