- Efficient chirality transfer in the Sml2-mediated cyclization of aldehydo β-alkoxyvinyl sulfoxides: Asymmetric synthesis of 3-hydroxyoxanes
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Stereoselective syntheses of 3-hydroxyoxanes were achieved via efficient chirality transfer in the Sml2-mediated cyclization reactions of aldehydo β-alkoxyvinyl sulfoxides.
- Jung, Jae Hoon,Kim, Yong Wook,Kim, Min Ah,Choi, Soo Young,Chung, Young Keun,Kim, Tae-Rae,Shin, Seokmin,Lee, Eun
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p. 3225 - 3228
(2008/02/11)
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- Stereoselective synthesis of tetrahydrofurans via formal [3+2]-cycloaddition of aldehydes and allylsilanes. Formal total synthesis of the muscarine alkaloids (-)-allomuscarine and (+)-epimuscarine
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The stereoselective synthesis of tetrahydrofurans was achieved by formal [3+2]-cycloaddition of allyl and crotylsilanes with α-triethylsilyloxy aldehydes. The scope of the reaction was examined by using different α-substituted aldehydes and different subs
- Angle, Steven R.,El-Said, Nahla A.
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p. 3608 - 3613
(2007/10/03)
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- Practical chiral route to muscarine and its three diastereomers
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A practical route to all possible stereoisomers of the muscarine alkaloids in optically pure forms has been developed starting from a readily accessible chiral starting material.
- Ohshiba,Yoshimitsu,Ogasawara
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p. 1067 - 1069
(2007/10/02)
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- Dichloromethylenation of Sugar γ-Lactones: a Stereospecific Synthesis of L-(+)-Muscarine and L-(+)-Epimuscarine Toluene-p-sulphonates
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Treatment of di-isopropylidene-D-mannono-1,4-lactone (3) with hexamethylphosphorous triamide-tetrachloromethane gave the dichloro-olefin (4), which was converted into the ketone (5) by treatment with lithium di-isopropylamide.Reduction with Raney nickel g
- Bandzouzi, Alphonse,Chapleur, Yves
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p. 661 - 664
(2007/10/02)
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- A Stereospecific Synthesis of (+)-Muscarine
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A stereospecific synthesis of (+)-muscarine (1) is described in which acid-catalysed cyclisation of D-mannitol gives 2,5-anhydro-D-glucitol, isolated as its 1,3-O-isopropylidene-4,6-dibenzoate (3); acid hydrolysis then tosylation gives the 1,3-di-O-tosyl derivative (7), converted by sodium methoxide-methanol into 2,5:3,4-dianhydro-1-tosyl-D-allitol (8).This epoxide with sodium bis-(2-methoxyethoxy)aluminium hydride gives 2,5-anhydro-1,4-dideoxy-d-ribo-hexitol (10) and its 1,3-dideoxy-isomer (11) (12:1).The former, with tosyl chloride then trimethylamine gives (+)-muscarine tosylate, also isolated as chloride and bromide salts.
- Mubarak, Azeez M.,Brown, Daniel M.
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p. 809 - 814
(2007/10/02)
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