Structure and reactivity Muscarine

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efficient synthesis of (+)-muscarine

the scheme below represents efficient way of synthesis of (+)-muscarine according scientists chan , li in canadian journal of chemistry in 1992. s-(−)-ethyl lactate (2)(figure 4) converted 2,6-dichlorobenzyl ether (3). diisobutylaluminium hydride (dibal) reduction of 2,6-dichlorobenzyl ether gives aldehyde (4). treatment of crude aldehyde allyl bromide , zinc powder in water nh4cl catalyst resulted in anti:syn mixture of 5a , 5b. treatment of 5a iodine in ch3cn @ 0 °c gives cyclized product 6a. treatment of 6a excess trimethylamine in ethanol gave (+)-muscarine (2s,4r,5s). similar reaction sequence 5b gave (+)-epimuscarine (7).



figure 4. scheme of synthesis of (+)-muscarine.


other syntheses

it can synthesized in various ways different substances, particularly 2,5-dimethyl-3-carboxymethyl flurane.








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