Tetrahedron Letters p. 8561 - 8564 (1996)
Update date:2022-08-04
Topics:
Bell, Andrew A.
Pickering, Lea
Watson, Alison A.
Nash, Robert J.
Griffiths, Rhodri C.
Jones, M. George
Fleet, George W.J.
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.
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