Base-catalyzed Diels-Alder reactions of 2H-pyran-2,5-diones: a mild approach to basiliolide B.
A new class of base-catalyzed Diels-Alder reactions of 2H-pyran-2,5-diones has been developed using catalytic amount of dicyclohexylmethylamine in tert-butyl alcohol. This method has been successfully employed for construction of the tricyclic core of basiliolide B at room temperature with good yields and exclusive endo selectivity.
Zhou
Xiongfei
X
Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen University Town, Xili, Shenzhen 518055, China.
Wu
Wanqing
W
Liu
Xiaozu
X
Lee
Chi-Sing
CS
D002384:Catalysis; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D053629:Thapsia / Q000737:chemistry*; D019284:Thapsigargin / Q000737:chemistry
D004791:Enzyme Inhibitors; D011714:Pyrans; D011753:Pyrones; C543083:basiliolide B; D019284:Thapsigargin