Juntaro Tanaka

The Reaction of Phenolic Compounds with Isoprenoids. Part VII.1) ortho-Prenylation of Phenol in the Presence of Alkali-Metal Catalysts

Abstract ortho-Prenylphenols and its derivatives occur frequently in plants and microorganism,2) and have been assumed to be essential intermediates in the biosynthesis of some natural products. ortho-Prenylphenols have been synthesized by the Friedel-Crafts reaction of prenyl alcohols or prenyl halides with phenols,3)-6) or by direct alkylation of phenols with polyprenyl halides in the alkaline media.7) These reactions had no

Synthesis of Grifolin and its Homologues1)

Abstract In regard to the synthesis of grifolin [I] which is an antibiotic fungal metabolite,2) the condensation of orcinol with farnesol and farnesyl bromide by toluene-p-sulphonic acid,3) oxalic acid,4) and others5,6) have been reported recently.

Simple Routes 5-Alkylamino-p-Menthene

Abstract The reactions of metalated aldimine with electrophiles have been widely used for the purpose of synthesis of several natural products1-3). In this communication, we wish to report simple synthetic methods for 5-alkylamino-p-menthene (1) using the metalated aldimine.

The Conversion of Isoprene-Carbon Tetrachloride Adducts in Alkali Medium

The reaction of isoprene-CCl4 adducts (a mixture of 1, 1, 1, 5-tetrachloro-3-methyl-3-pentene(1) and 1, 1, 1, 5-tetrachloro-4-methyl-3-pentene(2)) with alkali was studied. This reaction proceeds step-wise and the reactivity of the adduct depends on the position of the methyl group towards the trichleromethyl group. 1-Carbomethoxy 4 methoxy-2-methyl-1-butene(9) and 1-carbomethoxy-4-methoxy. 2-methyl-1-butene(10) were obtained from (1), while 1, 1-dichloro-5-methoxy-4 methyl-1, 3-pentadiene(6) was obtained from (2). Furthermore, the model compounds such as 1, 1, 1, 5-tetrachloro-3-pentene(11) and 1, 1, 1, 5-tetrachloro-3, 4-dimethyl3-pentene(12) were synthesized and the reations were tested.It is concluded that when the methyl group of the adduct is located at β-position towards the trichloromethyl group, the diene is converted to the chloroacetylenic compounds.