134312-41-7Relevant articles and documents
Total Synthesis and Assignment of the Absolute Configuration of (+)-Omphalic Acid
Chen, Renzhi,Qiu, Dongsheng,Lei, Xin,Niu, Yujie,Hua, Yuhui,Peng, Huayu,Zeng, Tao,Zhang, Yandong
, p. 6972 - 6976 (2021)
Omphalane diterpenoids usually contain a cyclohexane-fused bicyclo[3.2.1]octane scaffold embedded with two continuous quaternary carbon centers, which pose considerable challenges to synthetic chemists. Herein, we reported the first total synthesis of omphalic acid with high stereochemical control, featuring an intermolecular Diels-Alder cycloaddition, ring reorganization through Criegee oxidative cleavage and programmed aldol condensations, conformationally controlled hydrogenation, and Pd-catalyzed carboxylation. The absolute configuration of omphalic acid was defined for the first time via the asymmetric total synthesis facilitated by a derivatization resolution protocol.
Intramolecular Cyclopropanation-Ring Fragmentation Leading to Spirocyclic Ring Construction: A Stereoselective Synthesis of β-Chamigrene
Adams, Julian,Lepine-Frenette, Carole,Spero, Denice M.
, p. 4494 - 4498 (2007/10/02)
The transannular cylopropanation of a keto carbene generated by Rh2(OAc)4 catalysis on a bicyclic dihydropyran nucleus provided a key oxatricyclic ketone intermediate for the synthesis of the spirocyclic ring construction.Selective fragmentation of
