TY - JOUR
T1 - Alpinigenine from Papaver bracteatum Lindl. Restricted rotation in an unusual oxidation product
AU - Lavie, David
AU - Berger-Josephs, Hana
AU - Yehezkel, Tamar
AU - Gottlieb, Hugo E.
AU - Levy, Elie C.
PY - 1981
Y1 - 1981
N2 - Alpinigenine (1) was isolated in relatively large amount from a type of Papaver bracteatum Lindl. from Iran. Oxidation of this alkaloid with Jones reagent produced a lactone function and, unexpectedly, converted the NMe into an NCHO, present as a mixture of rotamers. Crystallization afforded one pure component, which equilibrated in solution within 2 h. 13C N.m.r. spectroscopy was used to confirm these results and enabled an insight into the conformation in solution of the seven-membered rings in alpinigenine and its oxidation product. X-Ray analysis determined unambiguously the absolute configuration of alpinigenine.
AB - Alpinigenine (1) was isolated in relatively large amount from a type of Papaver bracteatum Lindl. from Iran. Oxidation of this alkaloid with Jones reagent produced a lactone function and, unexpectedly, converted the NMe into an NCHO, present as a mixture of rotamers. Crystallization afforded one pure component, which equilibrated in solution within 2 h. 13C N.m.r. spectroscopy was used to confirm these results and enabled an insight into the conformation in solution of the seven-membered rings in alpinigenine and its oxidation product. X-Ray analysis determined unambiguously the absolute configuration of alpinigenine.
UR - http://www.scopus.com/inward/record.url?scp=37049106019&partnerID=8YFLogxK
U2 - 10.1039/p19810001019
DO - 10.1039/p19810001019
M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???
AN - SCOPUS:37049106019
SN - 1472-7781
SP - 1019
EP - 1022
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
ER -