Syntheses of 2,4-dihydroxy- and 1,3-dihydroxy-8-methylphenanthrene-9,10-quinones and their bearing on the structure of denticulatol
作者:M. V. Sargent、David O'N. Smith
DOI:10.1039/j39700000329
日期:——
gave 2,4-dihydroxy-8-methylphenanthrene-9,10-quinone (III). A similar route gave 1,3-dihydroxy-8-methylphenanthrene-9,10-quinone. Neither quinone had properties corresponding to those reported for denticulatol.
(2-甲基苄基)三苯基溴化,、 3,5-二甲氧基苯甲醛和甲醇锂的Wittig反应得到3,5-二甲氧基-2'-甲基methyl(V),经光环脱氢得到2,4-二甲氧基-8-甲基菲(VI)。该菲 烯脱甲基,然后乙酰化得到2,4-二乙酰氧基-8-甲基菲(VII),其在三氧化铬上氧化和水解得到2,4-二羟基-8-甲基菲-9,10-醌(III)。类似的途径得到1,3-二羟基-8-甲基菲-9,10-醌。两种醌都没有与报道的树胶醇相对应的特性。