Journal of the Chemical Society. Perkin transactions I p. 82 - 87 (1981)
Update date:2022-07-30
Topics:
Dennif, Phillip
Macleod, Ian
Whiting, Donald A.
The deprotonation of trimethylsilylzingerone (13) by lithium di-isopropylamide at -78 deg C has been found to be regioselective (92 : 8 in favour of less-substituted enolate): the anion was condensed with alkanals and acyl imidazoles to give convenient syntheses of (+/-)-<2>-<10>- and -<12>-gingerols (1) and <4>-, <6>-, and <8>-gingerdiones (9).Similary, 3-methoxy-4-trimethylsilyloxybenzylideneacetone (17) gave the (+/-)-<2>-<10>-dehydrogingerols (8) and <4>-, <6>-, and <8>-dehydrogingerdiones (10).The aldol reaction to <6>-gingerol and methyl <6>-gingerol was also conducted through a vinyloxyborane or through the enol silyl ether (TiCl4 catalysis).Results of organoleptic assays on these compounds are discussed, and the relation between pungency in the gingerols and in capsaicin is commented on.The aldol method was also used to synthesise the natural β-ketols(+/-)-daphneolone (25) and (+/-)-hexahydrocurcumin (4).
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