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

Bell, A.A., Pickering, L., Watson, A.A., Nash, R.J., Griffiths, R.C., Jones, M.G.K.ORCID: 0000-0001-5002-0227 and Fleet, G.W.J. (1996) 2-Hydroxycastanospermines (dihydroxy-L-swainsonines) from octonolactones: Inhibition of naringinase (L-rhamnosidase). Tetrahedron Letters, 37 (47). pp. 8561-8564.

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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.

Item Type: Journal Article
Publisher: Elsevier Ltd
Copyright: © 1996 Elsevier Ltd.
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