Title: Mycelianamide
CAS Registry Number: 22775-52-6
CAS Name: (6S)-3-[[4-[[(2E)-3,7-Dimethyl-2,6-octadienyl]oxy]phenyl]methylene]-1,4-dihydroxy-6-methyl-2,5-piperazinedione
Molecular Formula: C22H28N2O5
Molecular Weight: 400.47
Percent Composition: C 65.98%, H 7.05%, N 7.00%, O 19.98%
Literature References: Antibiotic substance found in the mycelium of Penicillium griseofulvum: Anslow, Raistrick, Biochem. J. 25, 39 (1931); Oxford et al., ibid. 29, 1102 (1935); 33, 240 (1939); Oxford, Raistrick, ibid. 42, 323 (1948). Structure: Birch et al., J. Chem. Soc. 1956, 3717; Bates, Schauble, Tetrahedron Lett. 1963, 1683. Configuration: Gallina et al., Gazz. Chim. Ital. 94, 1301 (1964). Partial synthesis: Brown, Meehan, Aust. J. Chem. 21, 1581 (1968). Total synthesis: N. Shinmon et al., Chem. Commun. 1980, 1020.
Properties: Crystals from ethyl acetate, dec 170-172°. [a]19546 -217°; [a]19579 -182°. Weak acid. Freely soluble in acetone, dioxane; sparingly sol in other organic solvents; sol in aq sodium carbonate solution, but not in sodium bicarbonate soln. Quickly destroyed by acids and alkalies.
Optical Rotation: [a]19546 -217°; [a]19579 -182° |