Synthesis of (3S,5S) -quinuclidine-3,5-diol and of [3S- (3α,3aα,7aα) ]-octahydro-2-furo[2,3-c]pyridinol from D-arabinose
Vazquez-Tato, M.P.; Seijas, J.A.; Fleet, G.W.J.; Mathews, C.J.; Hemmings, P.R.; Brown, D.J.
Tetrahedron 51(3): 959-974
1995
ISSN/ISBN: 1464-5416 DOI: 10.1016/0040-4020(94)01009-o
Accession: 098607974
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Summary
The synthesis of (3S,5S)-quinuclidine-3,5-diol is achieved by an introduction of a 2 carbon chain at C-3 of D-arabinose, followed by joining the terminus of the chain extension to C-1 and C-5 of the sugar; the synthesis of [3S-(3α,3aα,7aα)]-octahydro-2-furo[2,3-c]pyridinol, a potential muscarine mimic, is described.References
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