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

Tohru Oishi, Toshihiro Iwakuma, Masahiro Hirama, Shô Itô

Research output: Contribution to journalArticle

59 Citations (Scopus)

Abstract

(+)-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.

Original languageEnglish
Pages (from-to)404-406
Number of pages3
JournalSynlett
Volume1995
Issue number5
DOIs
Publication statusPublished - May 1 1995
Externally publishedYes

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Swainsonine
Indolizidines
Osmium
Carbamates
Amides
Glutamic Acid

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Stereoselective Synthesis of (+)-Swainsonine and (-)-8,8a-Di-epi -swainsonine. / Oishi, Tohru; Iwakuma, Toshihiro; Hirama, Masahiro; Itô, Shô.

In: Synlett, Vol. 1995, No. 5, 01.05.1995, p. 404-406.

Research output: Contribution to journalArticle

Oishi, Tohru ; Iwakuma, Toshihiro ; Hirama, Masahiro ; Itô, Shô. / Stereoselective Synthesis of (+)-Swainsonine and (-)-8,8a-Di-epi -swainsonine. In: Synlett. 1995 ; Vol. 1995, No. 5. pp. 404-406.
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