Journal ArticleDOI
N-substituted pyrrolidin-3-ones as heterocyclic building blocks. Enantioselective synthesis of 8-epi- and 1,8,8a-triepi-castanospermine
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TLDR
In this paper, a new approach to the construction of polyhydroxy indolizidines was proposed and the application of this methodology to the synthesis of 8-epicastanospermine 11 and 1,8,8a-triepicASTN-permine 12 is described.Abstract:
Regioselective aldol reaction of dianion 1 with aldehyde 5 provides the basis of a new approach to the construction of polyhydroxy indolizidines and the application of this methodology to the synthesis of 8-epicastanospermine 11 and 1,8,8a-triepicastanospermine 12 is described.read more
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Book ChapterDOI
Simple indolizidine and quinolizidine alkaloids.
TL;DR: The present survey covers the literature from mid-1999 to the end of 2013; and in addition to aspects of the isolation, characterization, and biological activity of the alkaloids, much emphasis is placed on their total synthesis.
Journal ArticleDOI
Gold-catalyzed intermolecular oxidation of chiral homopropargyl sulfonamides: a reliable access to enantioenriched pyrrolidin-3-ones
TL;DR: A gold-catalyzed intermolecular oxidation of chiral homopropargyl sulfonamides has been developed, which provides a reliable access to synthetically useful chiral pyrrolidin-3-ones with excellent results by combining the chiral tert-butylsulfinimine chemistry and gold catalysis.
Journal ArticleDOI
A flexible approach to azasugars: asymmetric total syntheses of (+)-castanospermine, (+)-7-deoxy-6-epi-castanospermine, and (+)-1-epi-castanospermine.
TL;DR: The method constitutes the first realization of the challenging chiral synthons A and D and thus of the conceptually attractive retrosynthetic analysis shown in Scheme 1 in a highly enantioselective manner.
Journal ArticleDOI
Samarium diiodide promoted generation and asymmetric hydroxyalkylation of N,O-diprotected (3S)-3-pyrrolidinol 2-carbanions.
TL;DR: Application of the present method led to the formal asymmetric syntheses of (2R, 3S)-2-hydroxymethyl-3-pyrrolidinol (2) and (2S,3S)-3-hydroxyproline (12).
Journal ArticleDOI
A concise approach to (+)-1-epi-castanospermine
Tian-Jun Wu,Pei-Qiang Huang +1 more
TL;DR: In this paper, a concise enantioselective synthesis of (+)-1-epi-castanospermine (2) was described, which featured the use of chiral non-racemic tetramic acid derivative 5 as a synthetic equivalent of the challenging synthon A through a highly diasterelective vinylogous Mukaiyama type reaction.
References
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Journal ArticleDOI
Castanospermine, A 1,6,7,8-tetrahydroxyoctahydroindolizine alkaloid, from seeds of Castanospermum australe
Liza D. Hohenschutz,E.Arthur Bell,Phillip J. Jewess,David P. Leworthy,Robert J. Pryce,Edward Arnold,Jon Clardy +6 more
TL;DR: A new type of higher plant alkaloid, 1,6,7,8-tetrahydroxyoctahydroindolizine, designated castanospermine, has been isolated from the toxic seeds of the Australian legume Castanospermum australe.
Journal ArticleDOI
4-O-Benzyl-23-O-isopropylidene-L-threose: A useful building block for stereoselective synthesis of monosaccharides
TL;DR: The 4-O-Benzyl-23-Oisopropylidene-L-threose building block is a useful four-carbon building block for monosaccharide synthesis as discussed by the authors.
Journal ArticleDOI
Castanospermine in Alexa species
Robert J. Nash,Linda E. Fellows,Janet V. Dring,Charles H. Stirton,David M. Carter,David M. Carter,Mervyn P. Hegarty,E.Arthur Bell +7 more
TL;DR: Castanospermine, a physiologically active polyhydroxylated indolizidine alkaloid first isolated from seeds of Castanospermum australe, has been isolated from the dried pod of Alexa leiopetala and tentatively identified in seven other species of the same genus.
Journal ArticleDOI
Enantiomerically pure polyhydroxylated acyliminium ions. Synthesis of the glycosidase inhibitors (-)-swainsonine and (+)-castanospermine
S. A. Miller,A. R. Chamberlin +1 more
TL;DR: Two enantioselective methods of preparing representative examples of highly substituted hydroxy lactam that would be derived from a meso imide have been explored.
Journal ArticleDOI
Total, Asymmetric-Synthesis of (+)-Castanospermine, (+)-6-Deoxycastanospermine, and (+)-6-Deoxy-6-Fluorocastanospermine
TL;DR: In this paper, the dibenzyl acetal of (-)-(1S,4S)-7-oxabicyclo[2.2.1]hept-5-en-2-one ((-)-5) led to (+)-( 1S,5S,6S,7S,8R,8aS)-8-(benzyloxy)-6,7-epoxy-1-hydroxyoctahydroindolizidin -5-one) followed by reduction of the lactam and dep