title: Expeditious total syntheses of camptothecin and 10-hydroxycamptothecin.
abstract: New expeditious total syntheses of (S)-camptothecin (16% overall yield, 95% ee) and (S)-10-hydroxycamptothecin (14% overall yield, 99% ee) have been accomplished, respectively, starting from readily available and inexpensive materials. Development, optimization, and successful application of the cascade reaction consisting of a pyrrolidine-catalyzed Michael addition, an intramolecular aldol condensation, and an oxidative aromatization, the intramolecular oxa Diels-Alder cycloaddition, and the Sharpless asymmetric dihydroxylation make these two new syntheses more efficient and straightforward.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
authors.forename: Guan-Sai
authors.initials: GS
authors.lastname: Liu
authors.forename: Qing-Li
authors.initials: QL
authors.lastname: Dong
authors.forename: Yuan-Shan
authors.initials: YS
authors.lastname: Yao
authors.forename: Zhu-Jun
authors.initials: ZJ
authors.lastname: Yao
mesh_terms: D000588:Amines / Q000737:chemistry; D002166:Camptothecin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D002384:Catalysis; D007700:Kinetics
chemical_list: D000588:Amines; C028098:10-hydroxycamptothecin; D002166:Camptothecin