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Synlett 1995; 1995(5): 404-406
DOI: 10.1055/s-1995-5002
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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
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Publication Date:
31 December 2000 (online)

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(+)-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

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