136658-05-4Relevant academic research and scientific papers
Total Synthesis of Longeracinphyllin A
Li, Jian,Zhang, Wenhao,Zhang, Fei,Chen, Yu,Li, Ang
supporting information, p. 14893 - 14896 (2017/10/31)
The first and asymmetric total synthesis of longeracinphyllin A, a hexacyclic Daphniphyllum alkaloid, has been accomplished. A tetracyclic intermediate was prepared through silver-catalyzed alkyne cyclization and Luche radical cyclization. A phosphine-promoted [3 + 2] cycloaddition reaction was exploited to construct the sterically congested E ring bearing vicinal tertiary and quaternary centers. The cyclopentenone motif was assembled by using intramolecular Horner-Wadsworth-Emmons olefination. Raney Ni reduction delivered the tertiary amine from a thioamide precursor at a late stage.
Enantioconvergent access to the enantiomerically pure building blocks (+)-or (-)-4-hydroxy-3-methyl-2-cyclohexenone using a chemoenzymatic process
Palombo, Elie,Audran, Gérard,Monti, Honoré
, p. 403 - 406 (2007/10/03)
A convenient chemoenzymatic enantioconvergent access to enantiomerically pure (+)- or (-)-4-hydroxy-3-methyl-2-cyclohexenone is described using a one-pot two-step kinetic resolution-stereoinversion protocol followed by hydrolysis. The key step of the sequ
Straightforward enantioselective synthesis of both enantiomers of karahana lactone using a domino ring-closure sequence
Galano, Jean-Marie,Audran, Gérard,Monti, Honoré
, p. 7477 - 7481 (2007/10/03)
A straightforward enantioselective synthesis of both enantiomers of karahana lactone is described starting from enantiopure (R) or (S)-4-hydroxy-3-methyl-cyclohex-2-en-1-one. The key step of the sequence is an acid-induced domino reaction with three pathways running. Because of the first description of karahana lactone as a solid, the structure was secured by X-ray structural analysis. (C) 2000 Elsevier Science Ltd.
Concise total syntheses of the sesquiterpenoids (-)-homalomenol A and (-)-homalomenol B
Piers, Edward,Oballa, Renata M.
, p. 8439 - 8447 (2007/10/03)
The conjugate additions of the organocopper(I) reagents 22 and 27 to the enantiomerically homogeneous bicyclic enone 4 provided, after epimerization (NaOMe, MeOH) of the resultant product mixtures and appropriate chromatographic separations, the bicyclo[4.3.0]nonan-2-ones 24 and 28. Compounds 24 and 28 were readily converted, via two synthetic steps in each case, into the sesquiterpenoids (-)-homalomenols B (2) and A (1), respectively.
Synthesis of optically active cyclohexenol derivatives via enzyme catalyzed ester hydrolysis of 4-acetoxy-3-methyl-2-cyclohexenone
Polla, Magnus,Frejd, Torbjoern
, p. 5883 - 5894 (2007/10/02)
The optically active cyclohexenol derivatives 9a-9d, and 10a-10c are synthesized from (-)-6, which is obtained by enzymatic ester hydrolysis of racemic 8. Attempts towards the synthesis of the taxane skeleton are described.
