26462-74-8

Upstream product

• 58493-52-0 Methyl-4-(3-hydroxy-2.6-dimethylhexyl)cyclohex-1-en-carboxylat 
• 926-62-5 isobutylmagnesium bromide 
• 73484-31-8 (S)-4-((R)-2-Chlorocarbonyl-1-methyl-ethyl)-cyclohex-1-enecarboxylic acid methyl ester 
• 3431-68-3 diisobutylcadmium 
• 26462-81-7 (4S,8S)-p-menth-1-en-9-ol 
• 120019-20-7 4-((E)-1,5-Dimethyl-3-oxo-hex-1-enyl)-cyclohex-1-enecarboxylic acid methyl ester 
• 58475-12-0 4-[(R)-4-(5,5-Dimethyl-[1,3]dioxan-2-yl)-cyclohex-3-enyl]-2-isobutyl-2-methylsulfanyl-pentanoic acid 
• 26462-82-8 Toluene-4-sulfonic acid (S)-2-((S)-4-methyl-cyclohex-3-enyl)-propyl ester 
• 26462-80-6 (4S,8S)-p-menth-1-en-9-yl 3,5-dinitrobenzoate 
• 26462-83-9 (R)-3-((S)-4-Methyl-cyclohex-3-enyl)-butyronitrile 
• 186581-53-3 diazomethane 
• 26462-84-0 (2R)-(4-Methyl-3-cyclohexen-(1S)-yl)-6-methylheptan-4-on 
• 17844-04-1 2-(4-Cyan-4-hydroxy-cyclohexyl)-6-methyl-4-acetoxy-heptan 
• 17844-06-3 2-<4-Carboxy-Δ³-cyclohexenyl)-6-methyl-heptanol-(4) 

Downstream Products

• 6753-22-6 (S)-4-((R)-1,5-Dimethyl-3-oxo-hexyl)-cyclohex-1-enecarboxylic acid 
• 6753-22-6 todomatuic acid 
• 6753-22-6 (+/-)-Epitodomatusaeure 

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.