12-05679. Macusines [Archived]
Description and references
Isoln of A and B from Strychnos toxifera Schomb., Loganiaceae: A. R. Battersby et al., J. Chem. Soc. 1960, 1848. Structure of A: A. T. McPhail et al., Proc. Chem. Soc. London 1961, 223; of B: A. R. Battersby, D. A. Yeowell, ibid. 17. Config of A: M.-M. Janot et al., Bull. Soc. Chim. Fr. 1962, 1079. Crystal and molecular structure of A: A. T. McPhail et al., J. Chem. Soc. 1963, 1832. Sepn of C and abs config of A, B and C: A. R. Battersby, D. A. Yeowell, ibid. 1964, 4419.
Derivative
Macusine A.Nomenclature
CAS number: 6801-39-4
(16R)-17-Hydroxy-16-(methoxycarbonyl)-4-methylsarpaganium. [C22H27N2O3]+.
Properties
Chloride, prisms from ethanol + ether, mp 252°. [α]D25 57.5° (c = 1.45).Derivative
Macusine B.Nomenclature
CAS number: 6792-07-0
(4α)-17-Hydroxy-4-methylsarpaganium. [C20H25N2O]+.
Properties
Chloride, prisms from ethanol + ether, dec 248-249°. [α]D22 +15.6° (c = 1.21). uv max (water): 222, 273, 280, 291 nm (log ε 4.61, 3.84, 3.82, 3.74).Derivative
Macusine C.Nomenclature
CAS number: 6801-17-8
[C22H27N2O3]+.
Properties
The C-16 epimer of A. Chloride, crystals from ethanol + ether, dec 264-265°. [α]D24 60.8° (c = 2.13). uv max (water): 222, 272, 278, 289 nm (log ε 4.63, 3.88, 3.87, 3.76).Status
This monograph has been retired and is no longer subject to revision or update.