55353-16-7

Upstream product

• 37519-31-6 selin-11-en-4α-ol 
• 917-54-4 methyllithium 
• 4586-68-9 4-hydroxy-11⁽¹³⁾-eudesmen-12-oic acid 
• 917-64-6 methyl magnesium iodide 
• 4895-32-3 (4aR,7R,8aR)-4a-methyl-7-(1-methyl-1-hydroxyethyl)-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one 
• 157241-50-4 (+)-hedycaryol 
• 473-15-4 beta-eudesmol 
• 125196-77-2 eudesobovatol A 
• 639-99-6 elemol 
• 198994-29-5 Methanesulfonic acid (1S,2R,4aS,7S,8aR)-1-hydroxy-7-(1-hydroxy-1-methyl-ethyl)-1,4a-dimethyl-decahydro-naphthalen-2-yl ester 
• 198994-21-7 Methanesulfonic acid (1S,2S,4aS,7S,8aS)-7-isopropenyl-1,4a-dimethyl-decahydro-naphthalen-2-yl ester 
• 198994-20-6 Methanesulfonic acid (1S,2R,4aS,7S,8aS)-7-isopropenyl-1,4a-dimethyl-decahydro-naphthalen-2-yl ester 
• 198994-26-2 7βH-4α,14-epoxyeudesm-11-en-3α-ol 
• 198994-24-0 7βH-eudesma-4(14),11-dien-3α-ol 

Relevant academic research and scientific papers

Short and efficient hemisynthesis of α-eudesmol and cryptomeridiol

The aerial part of Dittrichia viscosa yielded two sesquiterpenes, isocostic acid (1) and ilicic acid (2), on multigram scale. These acids are appropriate starting materials for short and facile syntheses of α-eudesmol (5) and cryptomeridiol (6), natural products featuring anti-Alzheimer and anti-spasmodic properties. Compounds 5 and 6 were obtained in three steps in overall yields of 70% and 52%, respectively.

Intramolecular photocycloaddition of 2-cycloalkenyl-1,3-dioxin-4-one. Stereoselective synthesis of cis-eudesmane-4,11-diols

Two isomeric eudesmane-4,11-diols having a cis-decalin skeleton were synthesized via intramolecular photocycloaddition of 6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,3-dioxin-4-one. Comparison of their NMR spectra with the natural diol, isolated from the Pa

Enantioselective total syntheses of (-)-7βH-eudesmane-4α,11-diol and (+)-ent-7βH-eudesmane-4α,11-diol

The syntheses of (-)-7βH-eudesmane-4α,11-diol (2) and (+)-ent-7βH- eudesmane-4α,11-diol (ent2) were carried out starting from (-)- and (+)- dihydrocarvones. As a result, the structure, including absolute configuration, of the naturally occurring eudesmane-4,11-diol isolated from Pluchea arguta was determined to be (+)-ent-7βH-eudesmane-4α,11-diol (ent- 2).

Structures and spasmolytic activities of derivatives from sesquiterpenes of Alpinia speciosa and Alpinia japonica

Sesquiterpenes isolated from Alpinia speciosa and Alpinia japonica, and their derivatives were found to inhibit histamine- or barium chloride- induced contraction of excised guinea pig ileum when tested by the Magnus method. Major spasmolytic principles contained in those extracts were the sesquiterpenes, β-eudesmol, nerolidol, humulene epoxide II and 4α- hydroxydihydroagarofuran. Relationships between the chemical structures of the sesquiterpenes and their derivatives, and their spasmolytic activities were discussed.

SESQUITERPENES FROM LEAVES OF CRYPTOMERIA JAPONICA

Twenty-seven sesquiterpenes were isolated from leaves of Cryptomeria japonica.The new compounds included elem-1-en-4,11-diol, 11-acetoxyeudesman-4α-ol, eudesmane-5α,11-diol, 3-eudesmene-1β,11-diol, 1β-acetoxy-3-eudesmen-11-ol, 4-eudesmene-1β,11-diol, 1β-acetoxy-4-eudesmen-11-ol, 7-epi-4-eudesmene-1β,11-diol, 1β-acetoxy-4(15)eudesmen-11-ol.Their structures were determined by chemical and spectral methods. - Key words: Cryptomeria japonica; Taxodiaceae; leaves; sesquiterpenes.

Biotransformation of (+/-)-4,8-dimethylcyclodeca-3(E),7(E)-dien-1β-ol and (+)-Hedycaryol by Cichorium intybus

The biotransformation of the synthetic (E,E)-1,5-cyclodecadienol 5 and (+)-hedycaryol (11) by a root suspension of fresh chicory has been investigated.Incubation of 5 with a root suspension gave a 2:1 mixture of epimeric eudesmanediols 7a and 7b whereas 11 was selectively converted into cryptomeridiol (12).An explanation for the obtained results is proposed.

LABDANES FROM CRYPTOMERIA JAPONICA

Twenty-seven labdanes were isolated from the leaves of Cryptomeria japonica.The new compounds include 15-(2-oxopropylidene)labd-8(17)-en-19-oic acid, 15-oxolabda-8(17),13(E)-dien-19-oic acid, 7β-acetoxy-15-hydroxylabda-8(17),13E-dien-19-oic acid methyl ester, 14-hydroxy-15-norlabd-8(17)-en-19-oic acid methyl ester, 15-hydroxylabda-8(17),13Z-dien-19-oic acid methyl ester, 15,16-epoxylabda-13(16),14-dien-8α,19-diol, 8α-hydroxylabda-13(16),14-dien-19-yl p-methoxycinnamate, an ester formed by 15-acetylisocupressic acid and cryptomeridiol and an ether formed by isocupressic acid and cryptomeridiol. - Key words: Cryptomeria japonica; Taxodiaceae; leaves; diterpenes; labdane-type.

Structures of Eudesmagnolol and Eudeshonokiol, Novel Sesquiterpene-Neolignans Isolated from Magnolia obovata

Eudesmagnolol and eudeshonokiol, isolated from the bark of Magnolia obovata, have been assigned to unprecedented structures linked via an ether bond between sesquiterpene, eudesmol, and neolignans, magnolol and honokiol, respectively.

NOVEL NEUROTROPHIC SESQUITERPENE-NEOLIGNANS FROM MAGNOLIA OBOVATA

Novel sesquiterpene-neolignans, eudesobovatols A (1) and B (2) isolated from Magnolia obovata have been assigned structures on the basis of detailed spectroscopic analyses and chemical degradation, and eudesobovatol A has been found to exhibit neurotrophic activity at 1E-5 M 1E-7 M on neuronal cell culture system of fetal rat cerebral hemisphere.