289507-53-5Relevant academic research and scientific papers
Total synthesis of s (+)-curcuphenol, s (+)-curcuquinone and s (+)-curcuhydroquinone
Chinta, Ramakoteswara Rao,Harikrishna,Tulam, Vijaya Kumar,Bejjanki, Naveen Kumar,Mainkar, Prathama S.,Dubey
, p. 771 - 778 (2016/03/01)
A synthesis of (-)-curcuphenol, (-)-curcuquinone and (-)-curcuhydroquinone from o-valerolactone is described. The key steps include an Evans asymmetric methylation of 5-(benzyloxy)pentanoic acid (5), an oxidative aromatization of enone (11) and a regioselective oxidation of the phenol to o-quinone derivative with bis(trifluoro acetate)iodobenzene.
Application of the lithiation-borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes
Aggarwal, Varinder K.,Ball, Liam T.,Carobene, Simon,Connelly, Rickki L.,Hesse, Matthew J.,Partridge, Benjamin M.,Roth, Philippe,Thomas, Stephen P.,Webster, Matthew P.
supporting information; experimental part, p. 9230 - 9232 (2012/09/10)
The expedient enantioselective synthesis of 5 bisabolane sesquiterpenes has been achieved using a common, one-pot lithiation-borylation reaction of secondary benzylic carbamates and either protodeboronation or oxidation to give the natural products in few
Enantioselective total synthesis of heliannuols D and A
Takabatake, Kenya,Nishi, Izumi,Shindo, Mitsuru,Shishido, Kozo
, p. 1807 - 1808 (2007/10/03)
The enantioselective total synthesis of heliannuols D and A, which exhibits allelopathic activity, was discussed. The enantioselective total synthesis included base-mediated intramolecular cyclisation of phenolic epoxide. The analysis showed the preparation of configurationally defined enantiopure epoxide whose intramolecular aryl ether-forming reaction provided heliannuol D and/or heliannuol A.
Baker's yeast-mediated enantioselective synthesis of the bisabolane sesquiterpenes (+)-curcuphenol, (+)-xanthorrhizol, (-)-curcuquinone and (+)-curcuhydroquinone
Fuganti, Claudio,Serra, Stefano
, p. 3758 - 3764 (2007/10/03)
Fermenting baker's yeast converts the unsaturated aldehydes 5a-c into the saturated alcohols 6a-c, respectively. The microbial saturation of substrates adsorbed on a nonpolar resin proceeds in high chemical yields and shows complete enantioselectivity in the formation of the (S)-(+) isomers. Enantiopure 6a-c are versatile chiral building blocks for the synthesis of bisabolane sesquiterpenes. Their usefulness is shown in the preparation of (S)-(+)-curcuphenol, (S)-(+)-xanthorrhizol, (S)-(-)-curcuquinone and (S)-(+)-curcuhydroquinone. The Royal Society of Chemistry 2000.
