Stereoselective synthesis of (−)-8-epi-swainsonine starting with a chiral aziridine

An efficient synthesis of (−)-8-epi-swainsonine, starting from a commercially available 1-(R)-α-methylbenzylaziridine-2-methanol, was developed. The synthetic route utilizes stereocontrolled Sharpless asymmetric dihydroxylation governed by AD-mix-β followed by an aziridine ring opening-cyclization s...

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Bibliographic Details
Published inTetrahedron letters Vol. 54; no. 6; pp. 553 - 556
Main Authors Lee, Baeck Kyoung, Choi, Hwan Geun, Roh, Eun Joo, Lee, Won Koo, Sim, Taebo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 06.02.2013
Elsevier
Subjects
(−)-8-Epi-swainsonine
Allyl compounds
Asymmetry
Aziridine
Chemical reactions
Chemistry
Chemistry, Organic
Forming
Indolizidine alkaloids
Natural product
Physical Sciences
Precursors
Science & Technology
Sequences
Synthesis (chemistry)
Tetrahedrons
Total synthesis
Natural product
Indolizidine alkaloids
(−)-8-Epi-swainsonine
Total synthesis
Aziridine
ANALOGS
ALPHA-MANNOSIDASE
ASYMMETRIC SYNTHESES
SWAINSONA-CANESCENS
DIHYDROXYLATION
INHIBITION
RING-CLOSING METATHESIS
(-)-SWAINSONINE
(-)-8-Epi-swainsonine
NATURAL OCCURRENCE
ALKALOIDS
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Summary:An efficient synthesis of (−)-8-epi-swainsonine, starting from a commercially available 1-(R)-α-methylbenzylaziridine-2-methanol, was developed. The synthetic route utilizes stereocontrolled Sharpless asymmetric dihydroxylation governed by AD-mix-β followed by an aziridine ring opening-cyclization sequence to generate the five membered N-heterocyclic ring system present in the bicyclic target. A subsequent stereoselective allylation and piperidine ring forming cyclization then produced a precursor that was converted into (−)-8-epi-swainsonine.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.11.087