Expeditious total syntheses of camptothecin and 10-hydroxycamptothecin.
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.
Liu
Guan-Sai
GS
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Dong
Qing-Li
QL
Yao
Yuan-Shan
YS
Yao
Zhu-Jun
ZJ
D000588:Amines / Q000737:chemistry; D002166:Camptothecin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D002384:Catalysis; D007700:Kinetics
D000588:Amines; C028098:10-hydroxycamptothecin; D002166:Camptothecin