Synthesis of alkaloid 223A and a structural revision.
[structure: see text] Synthesis of alkaloid 223A has been achieved by sequential use of our original conjugate addition reaction to enaminoesters as the key step. The proposed structure for natural 223A (A, absolute configuration unknown) was revised to B, and the relative stereostructure was determined to be 5R*,6R*,8R*,9S* by the present synthesis.
Toyooka
Naoki
N
Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Sugitani 2630, 930-0194, Japan. toyooka@ms.toyama-mpu.ac.jp
Fukutome
Ayako
A
Nemoto
Hideo
H
Daly
John W
JW
Spande
Thomas F
TF
Garraffo
H Martin
HM
Kaneko
Tetsuo
T
D000818:Animals; D001001:Anura / Q000378:metabolism*; D007202:Indicators and Reagents; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
C104548:6,8-diethyl-5-propylindolizidine; D007202:Indicators and Reagents; D007212:Indolizines