26575-87-1

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 
• 186581-53-3 diazomethane 
• 26091-09-8 (+)-Epitodomatuic acid 
• 26666-83-1 (S)-2-Methyl-6-((R)-6-methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-heptan-4-one 
• 77614-31-4 (R)-3-(4-methyl-cyclohex-3-enyl)-but-3-enal 
• 128300-30-1 (S)-3-((R)-4-methylcyclohex-3-en-1-yl)butanal 
• 26462-77-1 (S)-2-Methyl-6-((R)-4-methyl-cyclohex-3-enyl)-heptan-4-one 
• 13835-75-1 (2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-1-ol 
• 26462-75-9 Toluene-4-sulfonic acid (R)-2-((R)-4-methyl-cyclohex-3-enyl)-propyl ester 
• 13835-32-0 (2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propyl 3,5-dinitrobenzoate 
• 58493-52-0 Methyl-4-(3-hydroxy-2.6-dimethylhexyl)cyclohex-1-en-carboxylat 
• 926-62-5 isobutylmagnesium bromide 

Downstream Products

• 17844-06-3 (R)-4-((1S:3Ξ)-3-hydroxy-1,5-dimethyl-hexyl)-cyclohexene-(1)-carboxylic acid-(1) 
• 58493-52-0 (R)-4-((1S,3Ξ)-3-hydroxy-1,5-dimethyl-hexyl)-cyclohex-1-enecarboxylic acid methyl ester 
• 26091-09-8 (+)-Epitodomatuic acid 
• 64314-14-3 Epijuvabiol 
• 80373-62-2 (+)-isoepijuvabiol 
• 132185-46-7 (+)-oxoepijuvabione 
• 6753-22-6 (+/-)-Epitodomatusaeure 
• 86279-09-6 4-(3-hydroxy-1,5-dimethyl-hexyl)-cyclohexane-carboxylic acid 

Relevant academic research and scientific papers

JUVABIONE ANALOGUES FROM TWO ABIES SACHALINENSIS TREES

Three new juvabione analogues were isolated from the wood of two Abies sachalinensis trees grown at Shikaoi and Aibetsu in Hokkaido, Japan, in addition to the known (+)-oxojuvabione first isolated in nature.Their structures were elucidated from spectral evidence.Key Word Index - Abies sachalinensis; Pinaceae; wood; sesquiterpenoid; juvabione analogue.

Baker's yeast mediated enantioselective synthesis of the bisabolene sesquiterpenes (+)-epijuvabione and (-)-juvabione

Fermenting baker's yeast converts the unsaturated aldehydes 7 and 11 into the saturated alcohols 8 and 12, respectively. The microbial saturation of the double bond proceeds in high chemical yields and the stereoselectivity of the reduction is strongly influenced by the E:Z ratio of the substrate. Enantiopure 8 and 12 are chiral building blocks for the synthesis of bisabolene sesquiterpenes and their usefulness is shown in the preparation of (+)-epijuvabione 1 and (-)-juvabione 3.

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.

A lipase-mediated route to (+)-juvabione and (+)-epijuvabione from racemic norcamphor

(+)-Juvabione and (+)-epijuvabione, natural sesquiterpenes exhibiting insect juvenile hormone activity, have been synthesized from (±)-norcamphor via the both enantiomeric intermediates having bicyclo[3.2.1]octane framework by employing a lipase-mediated kinetic ester-hydrolysis reaction and cyclopropane ring-expansion reaction as the key steps.

Stereo- and Enantio-controlled Synthesis of (+)-Juvabione and (+)-Epijuvabione from (+)-Norcamphor

(+)-Juvabione and (+)-epijuvabione, natural sesquiterpenes exhibiting insect juvenile hormone activity, have been synthesized with complete stereo- and enantio-control using (+)-norcamphor as the chiral precursor via both the enantiomeric bicyclooc

OCCURENCE OF EPIJUVABIONE-TYPE SESQUITERPENOIDS IN ABIES SACHALINENSIS

The wood of Abies sachalinensis from the Taisetsu mountain range of Japan afforded, in addition to 10 known compounds, seven new epijuvabione-type sesquiterpenoids, (+)-4'-dehydro-oxoepijuvabione, (-)-4'-dehydro-oxojuvabione, epijuvabienol ether, 5'-hydroxyepijuvabione, ar-dihydroxyepijuvabione, 3'-dehydroepijuvabi-5'-ol and 3'-isodihydroepitodomatuic acid.Their stereostructures were elucidated by chemical and spectral evidence. Key Word Index: Abies sachalinensis; Pinaceae; wood; epijuvabione anlogue; sesquiterpenoid.

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.