220106-58-1Relevant academic research and scientific papers
Formal total synthesis of (±)-herbertene-1,13-diol and (±)-α-herbertenol via Ireland ester Claisen rearrangement and RCM reaction sequence
Srikrishna,Lakshmi, B. Vasantha
, p. 1173 - 1175 (2007/10/03)
A combination of Ireland ester Claisen rearrangement and ring-closing metathesis (RCM) reactions has been employed for efficient formal total syntheses of herbertene-1,13-diol and α-herbertenol, sesquiterpenes containing two vicinal quaternary carbon atom
Total synthesis of (±)-1,13-herbertenediol, (±)-α-herbertenol and (±)-β-herbertenol
Srikrishna,Satyanarayana
, p. 1027 - 1030 (2007/10/03)
Total synthesis of α-herbertenol, β-herbertenol and 1,13-herbertenediol, employing a Claisen rearrangement and ring-closing metathesis as key reactions for the generation of the cyclopentane containing vicinal quaternary carbons, has been described.
Concise asymmetric synthesis of (-)-herbertenediol
Kita, Yasuyuki,Futamura, Junko,Ohba, Yusuke,Sawama, Yoshinari,Ganesh, Jnaneshuwara K.,Fujioka, Hiromichi
, p. 411 - 413 (2007/10/03)
The rearrangement of the optically active 3-aryl-2-methyl-2,3-epoxy tosylate (>98% ee) afforded the α-keto tosylate with a chiral quaternary carbon center and without loss of chirality. Reductive removal of the tosyloxy group gave the keto compound with a chiral quaternary carbon center, which was converted to (-)-herbertenediol (>98% ee).
Facile total synthesis of (±)-α-herbertenol, (±)-1,4-cuparenediol and (±)-cuparene-1,4-quinone
Pal, Ashutosh,Gupta, Pranab Dutta,Mukherjee, Debabrata
, p. 989 - 995 (2007/10/03)
The total syntheses of the bicyclic sesquiterpene phenols (±)-α-herbertenol (1) and (±)-1,4-cuparenediol (2) have been successfully accomplished involving copper-catalysed conjugate addition of Grignard reagents to unsaturated dinitriles and α,α-dimethyla
Facile total synthesis of (±)-α-herbertenol, (±)-α-cuparenone and (±)-HM-1 methyl ether involving alkylation of hindered esters
Pal, Ashutosh,Gupta, Pranab Dutta,Roy, Arnab,Mukherjee, Debabrata
, p. 4733 - 4734 (2007/10/03)
The total syntheses of (±)-α-herbertenol 1, (±)-α-cuparenone 4 and (±)-HM-1 methyl ether 3 have been successfully accomplished involving α,α- dimethylation of the esters 8a, 17 and 8b respectively as key steps.
1,5-diketones from 3,4-dihydropyranones: An application in the synthesis of (±)-α-herbertenol
Harrowven, David C.,Hannam, Joanne C.
, p. 9333 - 9340 (2007/10/03)
An approach to 1,5-diketones involving the addition of organolithium reagents to 3,4-dihydropyranones is described. Good yields are obtained when reactions are quenched with trimethylsilyl chloride prior to hydrolytic work up and the organolithium reagent contains a Lewis basic group adjacent to the carbon to lithium bond. The method has been applied in a short synthesis of the fungicidal sesquiterpene (±)-α-herbertenol.
A short synthesis of α-herbertenol featuring the use of a dihydropyranone as a 1,5-diketone synthon
Harrowven, David C.,Hannam, Joanne C.
, p. 9573 - 9574 (2007/10/03)
The paper describes a short synthesis of α-herbertenol. Key features are the addition of dihyropyranone 5 to an aryllithium to give 1,5-diketone 7; a titanium(O) mediated cyclisation of 7 to diol 8 and a sequential methylation of 8 to herbertenol methyl ether 9.
Total synthesis of herbertenediol, an isocuparane sesquiterpene isolated from liverworts
Fukuyama, Yoshiyasu,Kiriyama, Yuuko,Kodama, Mitsuaki
, p. 1261 - 1264 (2007/10/03)
Total synthesis of herbertenediol, an isocuparane-sesquiterpene possessing a potent anti-lipid peroxidation activity isolated from a liverwort, has been achieved via herbertenol using intramolecular Heck reaction as the key step.
