17015-46-2

Upstream product

• 67-56-1 methanol 
• 26462-78-2 (R)-4-(1,5-Dimethyl-3-oxo-hexyl)-cyclohex-1-enecarbaldehyde 
• 58475-12-0 4-[(R)-4-(5,5-Dimethyl-[1,3]dioxan-2-yl)-cyclohex-3-enyl]-2-isobutyl-2-methylsulfanyl-pentanoic acid 
• 926-62-5 isobutylmagnesium bromide 
• 73484-31-8 (S)-4-((S)-2-Chlorocarbonyl-1-methyl-ethyl)-cyclohex-1-enecarboxylic acid methyl ester 
• 120019-20-7 4-((E)-1,5-Dimethyl-3-oxo-hex-1-enyl)-cyclohex-1-enecarboxylic acid methyl ester 
• 86272-38-0 (S)-4-[(S)-2-(2-Isobutyl-[1,3]dithian-2-yl)-1-methyl-ethyl]-cyclohex-1-enecarboxylic acid methyl ester 
• 186581-53-3 diazomethane 
• 6753-22-6 (+/-)-Todomatusaeure 
• 72457-75-1 4-(methoxycarbonyl)-β-methylcyclohex-3-ene-1-propanoic acid 
• 68075-96-7 lithio-2-(2-methylpropyl)-1,3-dithiane 
• 86272-36-8 (S)-7-[(S)-2-(2-Isobutyl-[1,3]dithian-2-yl)-1-methyl-ethyl]-1,4-dioxa-spiro[4.5]decane 
• 86272-37-9 (S)-3-[(S)-2-(2-Isobutyl-[1,3]dithian-2-yl)-1-methyl-ethyl]-cyclohexanone 
• 86272-34-6 (R)-(S)-2-(1,4-Dioxa-spiro[4.5]dec-7-yl)-propan-1-ol 

Downstream Products

• 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.