Asymmetric synthesis of double bond isomers of the structure proposed for pyrinodemin A and indication of its structural revision.
Asymmetric synthesis of double bond isomers (+)-2 (delta(15',16')) and (+)-3 (delta(14',15')) of the structure (1) (delta(16',17')) proposed for pyrinodemin A, a cytotoxic bis-pyridine alkaloid with a unique cis-cyclopent[c]isoxazolidine moiety from a marine sponge, has been accomplished. Pyrinodemin A was indicated to be a 1:1 racemic mixture of 2 from comparison of C(18 )and chiral HPLC analysis for pyrinodemin A and the synthetic compounds as well as ESIMS data of oxidative degradation products of pyrinodemin A.
Ishiyama
Haruaki
H
Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.
Tsuda
Masashi
M
Endo
Tadashi
T
Kobayashi
Jun'ichi
J
D002851:Chromatography, High Pressure Liquid; D007536:Isomerism; D008954:Models, Biological; D008968:Molecular Conformation; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*
D010080:Oxazoles; D011725:Pyridines; C430117:pyrinodemin A