396102-19-5

Upstream product

• 134050-29-6 trifluoromethanesulfonic acid 2-methyl-3-oxocyclopent-1-enyl ester 
• 396102-17-3 (2,3-dimethoxy-5-methylphenyl)boronic acid 
• 765-69-5 2-Methylcyclopentane-1,3-dione 
• 68278-85-3 3-bromo-4,5-dimethoxy-toluene 
• 494-99-5 1,2-dimethoxy-4-methylbenzene 
• 22117-97-1 3-isobutoxy-2-methyl-2-cyclopenten-1-one 

Downstream Products

• 503269-52-1 (1R)-2-methyl-3-(2,3-dimethoxy-5-methyl)phenyl-2-cyclopenten-1-ol 
• 503269-61-2 (-)-(1R,2R,5R)-1-methyl-5-(2,3-dimethoxy-5-methyl)phenyl-6-oxabicyclo[3.1.0]hexan-2-ol 
• 503269-53-2 (1R,2R,5R)-1-methyl-5-(2,3-dimethoxy-5-methyl)phenyl-6-oxabicyclo[3.1.0]hex-2-yl 4-methylbenzenesulfonate 
• 503269-54-3 (1R,3R)-3-methyl-3-(2,3-dimethoxy-5-methyl)phenyl-2-oxocyclopentyl 4-methylbenzenesulfonate 
• 582321-60-6 (1R,2R)-1,2-dimethyl-2-(2,3-dimethoxy-5-methyl)phenylcyclopentanol 
• 503269-58-7 2-(2,3-dimethoxy-5-methyl)phenyl-1,2-dimethylbicyclo[3.1.0]hexane 
• 503269-55-4 (2R)-2-methyl-2-(2,3-dimethoxy-5-methyl)phenylcyclopentanone 
• 503269-57-6 (3S)-2,3-dimethyl-3-(2,3-dimethoxy-5-methyl)phenylcyclopent-1-ene 
• 222022-93-7 (1'S)-1,2-dimethoxy-5-methyl-3-(1',2',2'-trimethylcyclopentyl)benzene 
• 86996-95-4 (S)-5-methyl-3-(1,2,2-trimethylcyclopentyl)benzene-1,2-diol 
• 396102-16-2 3-(2',3'-dimethoxy-5'-methylphenyl)-2-methylcyclopent-2-enol 

Relevant academic research and scientific papers

The rearrangement of 2,3-epoxysulfonates and its application to natural products syntheses: Formal synthesis of (-)-aphanorphine and total syntheses of (-)-α-herbertenol and (-)-herbertenediol

The Lewis acid treatment of 2,3-epoxysulfonates with 2,3-dialkyl substituents or 2-alkyl-3-aryl substituents produced the rearrangement products via C3-cleavage of the oxirane ring in high yields. On the other hand, 2-aryl-3-alkyl-2,3-epoxysulfonates produced the products via C2-cleavage of the oxirane ring. The sulfonyloxy groups of the α-sulfonyloxy ketones, having a chiral benzylic quaternary carbon center obtained by the rearrangement of 2-alkyl-3-aryl-2,3-epoxysulfonates, were reductively eliminated to give the ketones with a chiral benzylic quaternary carbon center. The method was applied to the formal synthesis of (-)-aphanorphine and total syntheses of (-)-α-herbertenol and (-)-herbertenediol.

Concise asymmetric synthesis of (-)-herbertenediol

The rearrangement of the optically active 3-aryl-2-methyl-2,3-epoxy tosylate (>98% ee) afforded the α-keto tosylate with a chiral quaternary carbon center and without loss of chirality. Reductive removal of the tosyloxy group gave the keto compound with a chiral quaternary carbon center, which was converted to (-)-herbertenediol (>98% ee).

New route to herbertanes via a Suzuki cross-coupling reaction: Synthesis of herbertenediol

The synthesis of herbertenediol, a relevant member of the herbertane-type sesquiterpene family, is described. The synthesis is based on a new general approach to this group of sesquiterpenes where the herbertane skeleton is constructed using a Suzuki cross-coupling reaction and a [2,3]-sigmatropic Still-Wittig rearrangement as key synthetic steps.