A flexible approach for the asymmetric syntheses of hyacinthacines A2, A3 and structural confirmation of hyacinthacine A3.
A concise and flexible approach for the asymmetric syntheses of polyhydroxylated pyrrolizidine alkaloids hyacinthacines A(2) and A(3) has been developed using iterative reductive alkylation of O,O'-dibenzyltartarimide (5) as key steps. The ambiguity about the structure of synthetic hyacinthacine A(3) due to the differences in the NMR data of the synthetic material (2) and the natural product (hyacinthacine A(3)) was eliminated jointly by comprehensive 1D and 2D-NMR studies, and by analysis of the (1)H and (13)C NMR spectra of a mixed synthetic product and natural hyacinthacine A(3). The latter method also allowed a confirmation of the structure of the natural hyacinthacine A(3), and may be useful for structural confirmation of other hydroxylated alkaloids.
Liu
Wen-Jun
WJ
Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. China.
Ye
Jian-Liang
JL
Huang
Pei-Qiang
PQ
D000478:Alkylation; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D011763:Pyrrolizidine Alkaloids; C500284:hyacinthacine A2; C550762:hyacinthacine A3