Synthesis of the CDE/FG ring models of prymnesins: reassignment of the relative configuration of the E/F ring juncture.
[structure: see text] Synthesis of two diastereomeric models (3a and 3b) corresponding to the CDE/FG ring of prymnesins, polycyclic ether toxins isolated from the red tide phytoflagellate Prymnesium parvum, is described. Comparison of the (1)H and (13)C NMR data for each compound with those reported for prymnesins suggests that the earlier stereochemical assignment of the E/F ring juncture needs to be revised.
Sasaki
Makoto
M
Graduate School of Life Sciences, Tohoku University, Tsutsumidori-amamiya, Aoba-ku, Sendai 981-8555, Japan. masasaki@bios.tohoku.ac.jp
Ebine
Makoto
M
Takagi
Hiroyuki
H
Takakura
Hiroyuki
H
Shida
Takeshi
T
Satake
Masayuki
M
Oshima
Yasukatsu
Y
Igarashi
Tomoji
T
Yasumoto
Takeshi
T
D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D061065:Polyketides; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism
D004987:Ethers; D006027:Glycosides; D006576:Heterocyclic Compounds, 4 or More Rings; D008387:Marine Toxins; D061065:Polyketides; D011714:Pyrans; C440216:prymnesin 1; C440215:prymnesin 2