201207-46-7

Upstream product

• 108-12-3 isopentanoyl chloride 
• 621-23-8 1,2,3-trimethoxybenzene 
• 101032-04-6 1-(2,4,6-trimethoxyphenyl)-3-methylbutan-1-one 

Downstream Products

• 219954-51-5 2,4,6-trimethoxy-5-(3-methyl-butyl)-isophthalic acid dimethyl ester 
• 335305-20-9 2,4,6-Trimethoxy-5-((E)-3-methyl-but-1-enyl)-isophthalic acid dimethyl ester 
• 335305-22-1 [3-Hydroxymethyl-2,4,6-trimethoxy-5-((E)-3-methyl-but-1-enyl)-phenyl]-methanol 
• 335305-17-4 2,4,6-Trimethoxy-5-((E)-3-methyl-but-1-enyl)-benzene-1,3-dicarbaldehyde 
• 219954-50-4 1,3-dibromo-2,4,6-trimethoxy-5-(3-methyl-butyl)-benzene 
• 219954-49-1 2-(3-methylbutyl)-1,3,5-trimethoxybenzene 
• 335305-18-5 (E)-1,3,5-trimethoxy-2-(3-methyl but-1-enyl)benzene 

Relevant academic research and scientific papers

The First Total Synthesis of Grandinal, a New Phloroglucinol Derivative Isolated from Eucalyptus grandis

The first total synthesis of grandinal (1) is accomplished by biomimetic cycloaddition of the jensenone derivative (2) and the o-quinone methide (3) generated by oxidation of grandinol (4).

Total synthesis of (-)-macrocarpal C. Stereoselective coupling reaction with a novel hexasubstituted benzene Cr(CO)3 complex as a biomimetic chiral benzyl cation equivalent

The first total synthesis of (-)-macrocarpal C (3) is described. The synthesis features a highly stereoselective coupling reaction of silyldienol ether 6 with biomimetic benzyl cation species (R)- and (S)-B, which were generated from novel hexasubstituted benzene chromium tricarbonyl complexes (R)- and (S)-17. At the final step of the total synthesis, we developed the tris-O-demethylation of macrocarpal C trimethyl ether 34 under basic conditions using lithium p-thiocresolate. Moreover, spectroscopic evidence shows that the synthetic (-)-3 is identical to natural macrocarpal G (4).

First stereoselective total synthesis of macrocarpal C: Structure elucidation of macrocarpal G

The first stereoselective total synthesis of macrocarpal C is achieved via a coupling reaction of a silyl dienol ether with a novel hexasubstituted benzene chromium tricarbonyl complex as an optically active benzyl cation equivalent, thereby clarifying the identity of macrocarpal C and G.