Macusines
Title: Macusines
Literature 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 Type: Macusine A
CAS Registry Number: 6801-39-4
CAS Name: (16R)-17-Hydroxy-16-(methoxycarbonyl)-4-methylsarpaganium
Molecular Formula: [C22H27N2O3]+
Properties: Chloride, prisms from ethanol + ether, mp 252°. [a]D25 -57.5° (c = 1.45).
Melting point: mp 252°
Optical Rotation: [a]D25 -57.5° (c = 1.45)
 
Derivative Type: Macusine B
CAS Registry Number: 6792-07-0
CAS Name: (4a)-17-Hydroxy-4-methylsarpaganium
Molecular Formula: [C20H25N2O]+
Properties: Chloride, prisms from ethanol + ether, dec 248-249°. [a]D22 +15.6° (c = 1.21). uv max (water): 222, 273, 280, 291 nm (log e 4.61, 3.84, 3.82, 3.74).
Optical Rotation: [a]D22 +15.6° (c = 1.21)
Absorption maximum: uv max (water): 222, 273, 280, 291 nm (log e 4.61, 3.84, 3.82, 3.74)
 
Derivative Type: Macusine C
CAS Registry Number: 6801-17-8
Molecular Formula: [C22H27N2O3]+
Properties: The C-16 epimer of A. Chloride, crystals from ethanol + ether, dec 264-265°. [a]D24 -60.8° (c = 2.13). uv max (water): 222, 272, 278, 289 nm (log e 4.63, 3.88, 3.87, 3.76).
Optical Rotation: [a]D24 -60.8° (c = 2.13)
Absorption maximum: uv max (water): 222, 272, 278, 289 nm (log e 4.63, 3.88, 3.87, 3.76)
 
 
Status: This monograph has been retired and is no longer subject to revision or update.

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