TY - JOUR
T1 - Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine
AU - Hakansson, AE
AU - van Ameijde, J
AU - Horne, G
AU - Nash, RJ
AU - Wormald, MR
AU - Kato, A
AU - Besra, Gurdyal
AU - Gurcha, Sudagar
AU - Fleet, GWJ
PY - 2008/1/1
Y1 - 2008/1/1
N2 - Efficient syntheses are reported of the alpha-L-rhamnosidase inhibitors L-swainsonine [(1R,2S,8S,8aS)-octahydroindolizine1,2,8-triol], (6R)-C-methyl-L-swainsonine (IR,2S,6R,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol, (6S)-C-methyl-L-swainsonine (IR,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol and related 6-C-methyl hydroxycastanospermines [(IR,2S, 6R,7R,8R,8aR)-6-methyl-octahydroindolizine-1,2,6,7,8-pentaol and (IR,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol]. (6R)-C-Methyl- L-swainsonine [K-i=0.032 mu M] is a significantly more potent naringinase inhibitor than L-swainsonine [K-i = 0.45 mu M]. (c) 2007 Elsevier Ltd. All rights reserved.
AB - Efficient syntheses are reported of the alpha-L-rhamnosidase inhibitors L-swainsonine [(1R,2S,8S,8aS)-octahydroindolizine1,2,8-triol], (6R)-C-methyl-L-swainsonine (IR,2S,6R,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol, (6S)-C-methyl-L-swainsonine (IR,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol and related 6-C-methyl hydroxycastanospermines [(IR,2S, 6R,7R,8R,8aR)-6-methyl-octahydroindolizine-1,2,6,7,8-pentaol and (IR,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol]. (6R)-C-Methyl- L-swainsonine [K-i=0.032 mu M] is a significantly more potent naringinase inhibitor than L-swainsonine [K-i = 0.45 mu M]. (c) 2007 Elsevier Ltd. All rights reserved.
U2 - 10.1016/j.tetlet.2007.10.142
DO - 10.1016/j.tetlet.2007.10.142
M3 - Article
SN - 0040-4039
VL - 49
SP - 179
EP - 184
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 1
ER -