52730-11-7Relevant academic research and scientific papers
Total Synthesis of (+)-Granatumine A and Related Bislactone Limonoid Alkaloids via a Pyran to Pyridine Interconversion
Schuppe, Alexander W.,Zhao, Yizhou,Liu, Yannan,Newhouse, Timothy R.
supporting information, p. 9191 - 9196 (2019/06/17)
We report the first total synthesis of (+)-granatumine A, a limonoid alkaloid with PTP1B inhibitory activity, in ten steps. Over the course of this study, two key methodological advances were made: a cost-effective procedure for ketone α,β-dehydrogenation using allyl-Pd catalysis, and a Pd-catalyzed protocol to convert epoxyketones to 1,3-diketones. The central tetrasubstituted pyridine is formed by a convergent Knoevenagel condensation and carbonyl-selective electrocyclization cascade, which was followed by a direct transformation of a 2H-pyran to a pyridine. These studies have led to the structural revision of two members of this family.
Synthetic Studies on Terpenoid Compounds. Part 14. Total Synthesis of Pyroangolensolide
Tokoroyama, Takashi,Fukuyama, Yoshiyashu,Kotsuji, Yasuhito
, p. 445 - 450 (2007/10/02)
4.8-Dimethyl-1,4,5,6,7,7a-hexahydroinden-2-one (7), obtained by Wichterle annelation of 2,6-dimethylcyclohexanone, was converted into 1-hydroxy-5,8-dimethyl-1,7,8,9-tetrahydro-3H-2-benzopyran-3-one (26).Treatment of compound (26) with 3-lithiofuran afforded pyroangolensolide (1) together with its diastereomer (4).
