Title: Narbomycin
CAS Registry Number: 6036-25-5
CAS Name: 12-Deoxypicromycin
Molecular Formula: C28H47NO7
Molecular Weight: 509.68
Percent Composition: C 65.98%, H 9.29%, N 2.75%, O 21.97%
Literature References: Antibiotic substance produced by Streptomyces narbonensis from soil near Cannes, France: Corbaz et al., Helv. Chim. Acta 38, 935 (1955). Structure: Prelog et al., ibid. 45, 4 (1962). Stereochemical studies: Rickards, Smith, Tetrahedron Lett. 1970, 1025; H. Ogura et al., J. Am. Chem. Soc. 97, 1930 (1975); eidem, Tetrahedron 37, Suppl. 1, 165 (1981). Isoln and structure of the aglycone narbonolide: Hori et al., Chem. Commun. 1971, 304. Synthesis of narbonolide: T. Kaiho et al., J. Org. Chem. 47, 1612 (1982).
Properties: Crystals from ether + petr ether, mp 113.5-115°. [a]D20 +68.5° (c = 1.35 in chloroform). uv max (abs ethanol): 225, 286 nm (log e 4.06, 2.23). LD50 s.c. in mice: 500 mg/kg (Corbaz).
Melting point: mp 113.5-115°
Optical Rotation: [a]D20 +68.5° (c = 1.35 in chloroform)
Absorption maximum: uv max (abs ethanol): 225, 286 nm (log e 4.06, 2.23)
Toxicity data: LD50 s.c. in mice: 500 mg/kg (Corbaz) |