Isolation and complete structural assignment of Lycopodium alkaloid cernupalhine A: theoretical prediction and total synthesis validation.
Cernupalhine A (1) is a trace Lycopodium alkaloid (0.7 mg) possessing a new C17N skeleton with an unusual hydroxydihydrofuranone motif newly isolated from Palhinhaea cernua L. Its complete structural assignment, including absolute stereochemistry, was established through a combination of high-field NMR techniques and computational methods and further unequivocal confirmation by the first asymmetric total synthesis. Following the first total synthesis of lobscurinine (3), 1 was achieved via regio- and stereoselective cyanide ion addition and subsequent acid treatment.
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, P. R China.
Liao-Bin
LB
Dong
Ya-Nan
YN
Wu
Shi-Zhi
SZ
Jiang
Xing-De
XD
Wu
Juan
J
He
Yu-Rong
YR
Yang
Qin-Shi
QS
Zhao
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification*; D032502:Lycopodium / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
D000470:Alkaloids; C000589533:cernupalhine A