First total synthesis of louisianin A.
The first total synthesis of louisianin A, 4-allyl-6,7-dihydro-1-hydroxycyclopenta[c]pyridin-5-one, is achieved from 2-chloro-4-cyanopyridine 5 via seven steps in an overall 24% yield. The key step is a cyclization-decarboxylation sequence toward the formation of a cyclopentenone ring.
Chang
Ching-Yao
CY
Department of Biotechnology and Bioinformatics, Asia University, Wufeng, Taichung, 413, Taiwan, Republic of China. cychang@asia.edu.tw
Liu
Hui-Ming
HM
Chow
Tahsin J
TJ
D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry
D000498:Allyl Compounds; D011725:Pyridines; C096930:louisianin A