Efficient total synthesis of (S)-14-azacamptothecin.
An efficient total synthesis of (S)-14-azacamptothecin has been accomplished in 10 steps and 56% overall yield from 5H-pyrano[4,3-d]pyrimidine 8. A mild Hendrickson reagent-triggered intramolecular cascade cyclization, a highly enantioselective dihydroxylation, and an efficient palladium-catalyzed transformation of an O-allyl into N-allyl group are the key steps in the synthesis. This work provides a much higher overall yield than the previous achievement and shows sound flexibility for the further applications that will lead to new bioactive analogues.
Liu
Guan-Sai
GS
Nanjing National Laboratory of Microstructures, School of Chemistry and Chemical Engineering, Nanjing University, 22 Hankou Road, Nanjing, Jiangsu 210093, China.
Yao
Yuan-Shan
YS
Xu
Peng
P
Wang
Shaozhong
S
Yao
Zhu-Jun
ZJ
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis*; D002166:Camptothecin / Q000031:analogs & derivatives / Q000138:chemical synthesis; D018360:Crystallography, X-Ray; D003500:Cyclization; D015394:Molecular Structure; D013237:Stereoisomerism
D000972:Antineoplastic Agents, Phytogenic; D002166:Camptothecin