40992-09-4

Upstream product

• 1195-09-1 5-methyl-2-methoxyphenol 
• 621-59-0 isovanillin 

Downstream Products

• 302321-76-2 4-bromo-6,6-dimethoxy-3-methyl-2,4-cyclohexadien-1-one 
• 486413-44-9 2-methoxy-5-methyl-4-trimethylsilanyl-phenol 

Relevant academic research and scientific papers

INDOLINE DERIVATIVES

Compounds of Formula (I) are disclosed and methods of treating viral infections with compositions comprising such compounds.

NEW THIENOPYRIMIDINE DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Compounds of formula (I): wherein R1, R2, R3, R4, R5, R6, R7, R12, X, A and n are as defined in the description.

Concise synthesis of the Hasubanan Alkaloid (±)-cepharatine A using a Suzuki coupling reaction to effect o,p -phenolic coupling

Suzuki coupling of 10 and 11 resulted in 9, which was O-alkylated to provide 12. Treatment of 12 with CsF in DMF resulted in the formation of the completed core structure 13 in a single step. Reductive amination of 13 completed the synthesis of (±)-cepharatine A, 4.

Intermolecular Diels-Alder reactions of brominated masked o-benzoquinones with electron-deficient dienophiles. A detour method to synthesize bicyclo[2.2.2]octenones from 2-methoxyphenols

Intermolecular Diels-Alder reactions of masked o-benzoquinones, i.e., 6,6-dimethoxy-2,4-cyclohexadienones 5-7 and 21-24 generated from 2-methoxyphenols 1-3 and 17-20, respectively, with electron-deficient dienophiles leading to highly functionalized bicyclo[2.2.2]octenones are described. The masked o-benzoquinones (MOBs) 5-7 underwent Diels-Alder cycloadditions with methyl acrylate, methyl methacrylate, and methyl vinyl ketone to provide bicyclo[2.2.2]octenones 13a-c to 15a-c (direct method) in low to moderate yields with the concomitant formation of considerable amounts of dimers 9-11. To retard dimerization and to improve the yields of the requisite bicyclo[2.2.2]octenones, a detour method comprised of sequential bromination of 2-methoxyphenols 1-4, oxidation and Diels-Alder reaction, and debromination has been developed. The oxidation of bromophenols 17-20 produced MOBs 21-24 which are stable enough to be isolated. The MOBs 21-24 underwent cycloaddition with electron-deficient dienophiles in a very efficient manner to afford the corresponding cycloadducts 25a-c to 28a-c in good to high yields without self-dimerization. When the cycloadducts 25a-c to 28a-c were treated with either Bu3SnH/AIBN or tributylammonium formate-palladium reagent, the corresponding debrominated products 13a-c to 16a-c were obtained in high to excellent yields. In general, the cycloadducts 13a-c to 15a-c were obtained in 20-40% higher yields via the detour method than those via the direct method. In both routes, the Diels-Alder reactions proceeded in a highly regio- and stereoselective manner to furnish a single cycloadduct in each case.

A new and highly stereoselective approach to cis-clerodanes

A new and highly stereoselective approach to cis-clerodanes and its application to the synthesis of (±)-2 is described.

Synthesis of stable bromo-substituted masked o-benzoquinones and their application to the synthesis of bicyclo[2.2.2]octenones

Preparation of stable equivalents of some unstable masked o-benzoquinones and their use in the preparation of bicyclo[2.2.2]octenones is described.