51371-15-4Relevant academic research and scientific papers
Synthesis and anti-plasmodial activity of 8β, 13β- Dihydroxypodocarpane derivatives
Young, Ryan M.,Popplewell, Wendy L.,Caira, Mino R.,Van Zyl, Robyn L.,Davies-Coleman, Michael T.
, p. 18 - 23 (2011/05/04)
8β,13β-Dihydroxypodocarpane and eight C-13 substituted derivatives were prepared from the precursor 8bhydroxy-13-podocarpanone synthesised from the naturally occurring diterpene (+)-manool. The synthetic compounds exhibited a range of anti-plasmodial activities (IC50 1-29 μM) and only induced minimal haemolysis of erythrocytes at concentrations 50 and 100 μM. No changes in the morphology of erythrocytes were detected at sub-haemolytic concentrations.
Butenolide annelations using a manganese(III) oxidation. A synthesis of jolkinolide E
Demir, Ayhan S.,Tanyeli, Cihangir,Akguen, Huelya,Caliskan, Zerrin,Oezguel, Emine
, p. 423 - 427 (2007/10/02)
A general procedure was developed for the annelation of a butenolide to an enone that highlighted a manganese(III) oxidation of an enone.The merit of this procedure was illustrated in a synthesis of (-)-jolkinolide E, ent-1, from (+)-manool 11.A potassium permanganate-mediated degradation of 11 and dehydration of an intermediate β-hydroxyketone 12 according to a literature procedure afforded a tricyclic enone 13.Oxidation of 13 with manganese(III) acetate and chloropropionic acid regio- and stereoselectively furnished a C-12α chloropropionyl ester 14.An Arbuzov reaction of 14 with triethylphosphite and an intramolecular Horner-Emmons cyclization of the resulting phosphonate 15 gave (-)-jolkinolide E, the structure of which was investigated in detail by NMR.This methodology was also applied to 4,4-dimethylcyclohex-2-en-1-one.This overall approach offers a general solution to the problem of butenolide annelation to enones. - Key words: (-)-jolkinolide E / manganese(III) acetate oxidation / butenolide annelation.
Ring Opening of Acetal III (8,13:13,17-Diepoxy-14,15-dinorlabdane) and the Synthesis of Potential Odorants Derived from Manool
Grant, Peter K.,Hanton, Lyall R.,Lynch, Gregory P.,Robinson, Ward T.,Wong Gordon
, p. 71 - 90 (2007/10/02)
A novel ring opening of the acetal III (2) (8,13:13,17-diepoxy-14,15-dinorlabdane) with boron trifluoride/acetic anhydride led to the synthesis of acetals (16), (18)-(20) and (25)-(27) functionalized at C 12.The attempted ring opening of the hydroxy acetal (28) produced the dimer (32).Also prepared were the cyclic ethers (36), (38) and (39), none of which, however, exhibited significant ambergris-type odours.
