721959-60-0Relevant articles and documents
Two contrasting asymmetric approaches to muscarine based on 5-endo-trig cyclisations
Knight, David W.,Shaw, Duncan E.,Staples, Emily R.
, p. 1973 - 1982 (2007/10/03)
5-endo-trig cyclisation of the (Z)-hydroxyalkenoate 17 using iodine as the electrophile gave a good yield of the β-hydroxytetrahydrofuran 18, probably via the corresponding iodohydrin. A variety of one-carbon degradation methods were then used to generate precursors to (-)-muscarine (25d). An alternative strategy featured control of a 5-endo-trig iodocyclisation by an allylic hydroxyl group, which can be used for the highly stereocontrolled synthesis of hydroxy-iodotetrahydrofurans 28. Application of this strategy to the (Z)-alkenediol derivative 38 led to an excellent yield of the tetrahydrofuran 39 when iodine monobromide was used as the electrophile. Two simple and efficient transformations then gave the (+)-muscarine precursor 40b. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
