3-Hydroxymuscarines from L-Rhamnose
1993; Elsevier BV; Volume: 49; Issue: 16 Linguagem: Inglês
10.1016/s0040-4020(01)90162-0
ISSN1464-5416
AutoresSimon J. Mantell, Peter S. Ford, David J. Watkin, George W. J. Fleet, David Brown,
Tópico(s)Chemical synthesis and alkaloids
ResumoNo protection is necessary for the synthesis of the muscarine analogue 3R-3-hydroxymuscarine from L-rhamnose; a sole silyl ether protecting group is required for the synthesis of 3S-3-hydroxymuscarine. Efficient construction of the tetrahydrofuran ring can be achieved either by ring contraction of the α-triflate of δ-rhamnonolactone, or by ring opening and closing of the α-triflate of γ-rhamnonolactone.
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