Chlorosilphanol A and silphanepoxol, labdane diterpenes from Silphium perfoliatum.
Two carterochaetols, chlorosilphanol A and silphanepoxol, isolated from the leaves of Silphium perfoliatum were assigned structures 1 and 3, respectively, from spectral studies and with absolute stereochemistry established by X-ray crystallography of 1. Complete 1H- and 13C-nmr assignments for the parent compounds and their acetates 2 and 4 were made at high-field using 1D and 2D methods, and chlorosilphanol A was chemically converted via its acetate to silphanepoxol. Revision of structure for related carterochaetols in the literature is required, in particular with respect to the stereochemistry at C-12 and that of the side-chain.
Pcolinski
M J
MJ
Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Ohio State University, Columbus 43210-1291.
Doskotch
R W
RW
Lee
A Y
AY
Clardy
J
J
D002728:Chlorohydrins / Q000737:chemistry / Q000302:isolation & purification*; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification*; D004852:Epoxy Compounds / Q000737:chemistry / Q000302:isolation & purification*; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010946:Plants, Medicinal / Q000737:chemistry*
D002728:Chlorohydrins; D004224:Diterpenes; D004852:Epoxy Compounds; D005663:Furans; C089563:chlorosilphanol A; C089562:silphanepoxol