91139-52-5

Upstream product

• 103263-13-4 (+/-)-6t-hydroxymethyl-3,4-dimethyl-cyclohex-3-ene-r-carboxylic acid 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 99862-40-5 (+/-)-6t-bromomethyl-3,4-dimethyl-cyclohex-3-ene-r-carboxylic acid methyl ester 
• 6096-53-3 dimethyl trans-1,2-dimethylcyclohexene-4,5-dicarboxylate 

Relevant academic research and scientific papers

Enantioselective total syntheses of (-)-palau'Amine, (-)-axinellamines, and (-)-massadines

Dimeric pyrrole-imidazole alkaloids represent a rich and topologically unique class of marine natural products. This full account will follow the progression of efforts that culminated in the enantioselective total syntheses of the most structurally ornate members of this family: the axinellamines, the massadines, and palau'Amine. A bio-inspired approach capitalizing on the pseudo-symmetry of the members of this class is recounted, delivering a deschloro derivative of the natural product core. Next, the enantioselective synthesis of the chlorocyclopentane core featuring a scalable, catalytic, enantioselective Diels-Alder reaction of a 1-siloxydiene is outlined in detail. Finally, the successful divergent conversion of this core to each of the aforementioned natural products, and the ensuing methodological developments, are described.

Syntheses of isomerically pure reference octalins and hydrindanes

We describe herein the development of efficient and stereoselective synthetic routes to a range of cis- and trans-octalin and hydrindane target compounds.

Synthesis and Fungicidal Activity of Alicyclic Diamines

As part of an ongoing program of work on polyamine analogues, a number of alicyclic diamines were synthesized and examined for fungicidal activity. The alicyclic diamine 1,2-bis(aminomethyl)-4,5-dimethylcyclohexa-1,4-diene (BAD), synthesized as the dihydrochloride salt, controlled the important crop pathogen Erysiphe graminis f.sp hordei. Greatest control of E. graminis was achieved when BAD was applied 2 days postinoculation. The alicyclic diamines trans-4,5-bis(aminomethyl)-1,2-dimethylcyclohex-1-ene (trans-BAD) and the cis-isomer (cis-BAD), as well as 1,2-bis(amino-methyl)cyclopentene (BACP) and irons-1,2-bis(dimethylaminomethyl)cyclobutane (TCCBM), were also synthesized as their dihydrochloride salts. trans-BAD was found to possess greater fungicidal activity than the cis-isomer against E. graminis, while BACP and TCCBM both gave >80% control of powdery mildew infection. Since the powdery mildew fungus cannot be grown axenically, the effects of the alicyclic diamines on polyamine metabolism were examined using the oat leaf stripe pathogen, Pyrenophora avenae. BAD and derivatives had little effect on polyamine metabolism in the fungal pathogen P. avenae. It seems clear, therefore, that the antifungal activity of these derivatives may not be associated with altered polyamine metabolism.