73484-31-8

Upstream product

• 72457-74-0 (R)-4-((E)-(R)-3-Methoxy-1-methyl-allyl)-2-[(E)-2-phenyl-aziridin-1-ylimino]-cyclohexanecarboxylic acid methyl ester 
• 123376-87-4 (R)-2-Methanesulfonyloxy-4-((S)-1-methyl-allyl)-cyclohexanecarboxylic acid methyl ester 
• 123376-85-2 (R)-4-((S)-1-Methyl-allyl)-2-oxo-cyclohexanecarboxylic acid methyl ester 
• 123393-62-4 (R)-2-Hydroxy-4-((S)-1-methyl-allyl)-cyclohexanecarboxylic acid methyl ester 
• 123376-79-4 (S)-4-((R)-1-Methyl-allyl)-cyclohex-1-enecarboxylic acid methyl ester 
• 930-68-7 cyclohexenone 
• 72457-77-3 methyl 4-(3-methoxy-1-methyl-(E,Z)-2-propenyl)-1-cyclohexene-1-carboxylate 
• 72457-75-1 3-(methyl-4-carboxyl-3-cyclohexenyl)butanoic acid 
• 123376-87-4 (R)-2-Methanesulfonyloxy-4-((R)-1-methyl-allyl)-cyclohexanecarboxylic acid methyl ester 
• 123376-85-2 (R)-4-((R)-1-Methyl-allyl)-2-oxo-cyclohexanecarboxylic acid methyl ester 
• 123393-62-4 (R)-2-Hydroxy-4-((R)-1-methyl-allyl)-cyclohexanecarboxylic acid methyl ester 
• 123376-79-4 (S)-4-((S)-1-Methyl-allyl)-cyclohex-1-enecarboxylic acid methyl ester 
• 123376-75-0 (R*)-3-((R*)-but-3-en-2-yl)cyclohexan-1-one 
• 72457-75-1 4-(methoxycarbonyl)-β-methylcyclohex-3-ene-1-propanoic acid 

Downstream Products

• 17015-46-2 methyl (+/-)-rel-(4R)-4-[(1R)-1,5-dimethyl-3-oxoethyl]cyclohex-1-enecarboxylate 
• 16981-74-1 (+/-)-erythro-juvabione 

Relevant academic research and scientific papers

Application of the novel tandem process Diels-Alder reaction/Ireland-Claisen rearrangement to the synthesis of rac-juvabione and rac-epijuvabione

The novel tandem process Diels-Alder reaction/Ireland-Claisen rearrangement shows a high diastereoselectivity for the Ireland-Claisen rearrangement starting from the endo-product of the Diels-Alder reaction. Based on this mechanistic knowledge, the novel tandem process could be applied to the synthesis of rac-juvabione.

EFFICIENT STEREOSELECTIVE SYNTHESIS OF BOTH (+/-)-JUVABIONE AND (+/-)-EPI-JUVABIONE BY NEW EXTRACYCLIC STEREOCONTROL METHODOLOGY

The Hosomi-Sakurai reactions of E- and Z-crotylsilanes with cyclohexenone at -78 degC showed respectively high erythro and relatively low threo selectivities, modification of the silyl substituents giving a variable effect.In the reaction with Z-alkoxycrotylsilanes, the threo selectivity could be improved by the utilization of the kinetic difference between the diastereomeric products 4 and 5 to the secondary cyclization.Starting from 4 and 5 thus obtained, the syntheses of both (+/-)-juvabione and (+/-)-epi-juvabione have been respectively achieved in a concise way.