Title: Illudins
Literature References: Anti-tumor antibiotic substances produced by the poisonous basidiomycetes Clitocybe illudens (now called Omphalotus illudens): Anchel et al., Proc. Natl. Acad. Sci. USA 36, 300 (1950); 38, 927 (1952); and Lampteromyces japonicus: Nakanishi et al., Nature 197, 292 (1963); Endo et al., Chem. Commun. 1970, 309. Structure: McMorris, Anchel, J. Am. Chem. Soc. 87, 1594 (1965); Matsumoto et al., Tetrahedron 21, 2671 (1965); Tada et al., Chem. Pharm. Bull. 12, 853 (1964). Stereochemistry: Nakanishi et al., ibid. 856; Tetrahedron 21, 1231 (1965); Matsumoto et al., Bull. Chem. Soc. Jpn. 37, 1716 (1964). Abs config of illudin S: Harada, Nakanishi, Chem. Commun. 1970, 310. Total synthesis of illudin M: Matsumoto et al., J. Am. Chem. Soc. 90, 3280 (1968); Tetrahedron Lett. 1970, 1171; of illudin S: eidem, ibid. 1971, 2049. In vitro antitumor activity in human cancer cells: M. J. Kelner et al., J. Natl. Cancer Inst. 82, 1562 (1990).
Derivative Type: Illudin M
CAS Registry Number: 1146-04-9
CAS Name: (3¢S-trans)-2¢,3¢-Dihydro-3,6-dihydroxy-2¢,2¢,4¢,6¢-tetramethylspiro[cyclopropane-1,5¢-[5H]inden]-7¢(6¢H)-one
Molecular Formula: C15H20O3
Molecular Weight: 248.32
Percent Composition: C 72.55%, H 8.12%, O 19.33%
Properties: Rods, mp 120-122.5° (Matsumoto); from ethanol-water, mp 128-130° (McMorris). uv max (ethanol): 228, 318 nm (e 13900, 3600).
Melting point: mp 120-122.5° (Matsumoto); mp 128-130° (McMorris)
Absorption maximum: uv max (ethanol): 228, 318 nm (e 13900, 3600)
Derivative Type: Monoacetate
Molecular Formula: C17H22O4
Molecular Weight: 290.35
Percent Composition: C 70.32%, H 7.64%, O 22.04%
Properties: mp 75-76° from petr ether.
Melting point: mp 75-76° from petr ether
Derivative Type: Illudin S
CAS Registry Number: 1149-99-1
CAS Name: [2¢S-(2¢a,3¢b,6¢a)]-2¢,3¢-Dihydro-3¢,6¢-dihydroxy-2¢-(hydroxymethyl)-2¢,4¢,6¢-trimethylspiro[cyclopropane-1,5¢-[5H]inden]-7¢(6¢H)-one
Additional Names: lampterol; lunamycin (obsolete)
Molecular Formula: C15H20O4
Molecular Weight: 264.32
Percent Composition: C 68.16%, H 7.63%, O 24.21%
Properties: Needles from acetone, mp 124-126°. uv max (ethanol): 233, 319 nm (e 13200, 3600). Sol in polar organic solvents.
Melting point: mp 124-126°
Absorption maximum: uv max (ethanol): 233, 319 nm (e 13200, 3600)
Derivative Type: Diacetate
Molecular Formula: C19H24O5
Molecular Weight: 332.39
Percent Composition: C 68.66%, H 7.28%, O 24.07%
Properties: Crystals from petr ether, mp 99-100°. uv max (ethanol): 227, 313 nm (e 12900, 3400).
Melting point: mp 99-100°
Absorption maximum: uv max (ethanol): 227, 313 nm (e 12900, 3400)
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