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2-Hydroxycastanospermines (dihydroxy-L-swainsonines) from octonolactones: Inhibition of naringinase (L-rhamnosidase)
Journal article   Peer reviewed

2-Hydroxycastanospermines (dihydroxy-L-swainsonines) from octonolactones: Inhibition of naringinase (L-rhamnosidase)

A.A. Bell, L. Pickering, A.A. Watson, R.J. Nash, R.C. Griffiths, M.G.K. Jones and G.W.J. Fleet
Tetrahedron Letters, Vol.37(47), pp.8561-8564
1996
DOI: https://doi.org/10.1016/0040-4039(96)01956-9
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Abstract

Short syntheses of 2S-2-hydroxycastanospermine, and 2R- and 2S-2-hydroxy-6-epicastanospermine — in which there are 6 adjacent chiral centres and 8 contiguous carbon atoms containing functional groups from eight carbon sugar lactones — depend on efficient cyclisations to give piperidines with trans-acetonides as protecting groups. Inhibition of naringinase (L-rhamnosidase) by 2S-2-hydroxy-6-epicastanospermine and 2S-2-hydroxycastanospermine may be due to a structural resemblance to the unnatural L-(+)-swainsonine. Short efficient syntheses of the very highly oxygenated indolizidine alkaloids 1, 2 and 3 from readily available eight carbon sugar lactones are reported. 1 and 2 are weak inhibitors of naringinase (L-rhamnosidase) which may be due to their structural resemblance to unnatural L-(+)-swainsonine.

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Collaboration types
Domestic collaboration
Citation topics
2 Chemistry
2.1 Synthesis
2.1.1145 Iminosugar Synthesis
Web Of Science research areas
Chemistry, Organic
ESI research areas
Chemistry
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