81784-10-3Relevant articles and documents
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.
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
The rearrangement of 2,3-epoxysulfonates and its application to natural products syntheses: Formal synthesis of (-)-aphanorphine and total syntheses of (-)-α-herbertenol and (-)-herbertenediol
Kita, Yasuyuki,Futamura, Junko,Ohba, Yusuke,Sawama, Yoshinari,Ganesh, Jnaneshwara K.,Fujioka, Hiromichi
, p. 5917 - 5924 (2007/10/03)
The Lewis acid treatment of 2,3-epoxysulfonates with 2,3-dialkyl substituents or 2-alkyl-3-aryl substituents produced the rearrangement products via C3-cleavage of the oxirane ring in high yields. On the other hand, 2-aryl-3-alkyl-2,3-epoxysulfonates produced the products via C2-cleavage of the oxirane ring. The sulfonyloxy groups of the α-sulfonyloxy ketones, having a chiral benzylic quaternary carbon center obtained by the rearrangement of 2-alkyl-3-aryl-2,3-epoxysulfonates, were reductively eliminated to give the ketones with a chiral benzylic quaternary carbon center. The method was applied to the formal synthesis of (-)-aphanorphine and total syntheses of (-)-α-herbertenol and (-)-herbertenediol.
Stereoselective total syntheses of (±)-1,14-herbertenediol and (±)-tochuinyl acetate and facile total syntheses of (±)-α-herbertenol, (±)-β-herbertenol and (±)-1,4-cuparenediol
Paul, Tapas,Pal, Ashutosh,Gupta, Pranab Dutta,Mukherjee, Debabrata
, p. 737 - 740 (2007/10/03)
Stereoselective total syntheses of (±)-1,14-herbertenediol (7) and (±)-tochuinyl acetate (10) and facile total syntheses of (±)-α-herbertenol (2), (±)-β-herbertenol (3) and (±)-1,4-cuparenediol (8) have been successfully accomplished involving intramolecu
Total syntheses of neuroprotective mastigophorenes A and B
Fukuyama, Yoshiyasu,Matsumoto, Keiji,Tonoi, Yasutoshi,Yokoyama, Ritsuko,Takahashi, Hironobu,Minami, Hiroyuki,Okazaki, Hiroshi,Mitsumoto, Yasuhide
, p. 7127 - 7135 (2007/10/03)
(-)-Herbertenediol (3) which is regarded as a biosynthetic precursor of mastigophorenes A and B has been effectively synthesized from (R)-1,2-dimethyl-2-cyclopentene carboxylic acid by applying an intramolecular Heck reaction to the construction of the quaternary carbon center, and then horseradish peroxidase-catalyzed oxidative coupling of 3 has given rise to (-)-mastigophorenes A and B. Mastigophorenes A and B have been found to exhibit significant neuroprotective activity in primary cultures of fetal rat cortical neurons.
Enantioselective synthesis of herbertane sesquiterpenes: Synthesis of (-)-α-formylherbertenol
Abad, Antonio,Agullo, Consuelo,Cunat, Ana C.,Perni, Remedios H.
, p. 1607 - 1615 (2007/10/03)
The synthesis of 4-hydroxy-3-[(1S)-1,2,2-trimethylcyclopentyl]benzaldehyde [(-)-α-formylherbertenol 1], a herbertane-type sesquiterpene isolated from the leafy liverwort Herberta adunca, from β-cyclogeraniol is described. The synthesis is based on the previously described preparation of an enantiopure 1,2,2-trimethylcyclopentane synthon from which the characteristic aromatic moiety of 1 is elaborated, using a Robinson annulation and a palladium-catalysed methoxycarbonylation of an aryl triflate as key synthetic steps. The synthesis of the natural sesquiterpene (-)-α-herbertenol, also a natural sequiterpene, using the same methodology is also described. Copyright (C) 2000 Elsevier Science Ltd.
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.
