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

Tohru Oishi; Toshihiro Iwakuma; Masahiro Hirama; Shô Itô

doi:10.1055/s-1995-5002

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

Tohru Oishi, Toshihiro Iwakuma, Masahiro Hirama, Shô Itô

Research output: Contribution to journal › Article › peer-review

60 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 language	English
Pages (from-to)	404-406
Number of pages	3
Journal	Synlett
Volume	1995
Issue number	5
DOIs	https://doi.org/10.1055/s-1995-5002
Publication status	Published - May 1995
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1055/s-1995-5002

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

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.",

author = "Tohru Oishi and Toshihiro Iwakuma and Masahiro Hirama and Sh{\^o} It{\^o}",

note = "Funding Information: The authors are in debt to the European Commission for the funding of several European research projects as well as all other partners and organisations for their support and co-operation. Publisher Copyright: {\textcopyright} 1995 Georg Thieme Verlag. All rights reserved.",

year = "1995",

month = may,

doi = "10.1055/s-1995-5002",

language = "English",

volume = "1995",

pages = "404--406",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

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T1 - Stereoselective Synthesis of (+)-Swainsonine and (-)-8,8a-Di-epi -swainsonine

AU - Oishi, Tohru

AU - Iwakuma, Toshihiro

AU - Hirama, Masahiro

AU - Itô, Shô

N1 - Funding Information: The authors are in debt to the European Commission for the funding of several European research projects as well as all other partners and organisations for their support and co-operation. Publisher Copyright: © 1995 Georg Thieme Verlag. All rights reserved.

PY - 1995/5

Y1 - 1995/5

N2 - (+)-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.

AB - (+)-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.

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U2 - 10.1055/s-1995-5002

DO - 10.1055/s-1995-5002

M3 - Article

AN - SCOPUS:0038975186

SN - 0936-5214

VL - 1995

SP - 404

EP - 406

JO - Synlett

JF - Synlett

IS - 5

ER -

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

Abstract

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