Description and 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
Illudin M.
Nomenclature
CAS number: 1146-04-9
(3′
S-trans)-2′,3′-Dihydro-3,6-dihydroxy-2′,2′,4′,6′-tetramethylspiro[cyclopropane-1,5′-[5
H]inden]-7′(6′
H)-one.
C
15H
20O
3; mol wt 248.32.
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 (ε 13900, 3600).Derivative
Illudin S.
Nomenclature
CAS number: 1149-99-1
[2′
S-(2′α,3′β,6′α)]-2′,3′-Dihydro-3′,6′-dihydroxy-2′-(hydroxymethyl)-2′,4′,6′-trimethylspiro[cyclopropane-1,5′-[5
H]inden]-7′(6′
H)-one; lampterol; lunamycin (obsolete).
C
15H
20O
4; mol wt 264.32.
C 68.16%, H 7.63%, O 24.21%.
Properties
Needles from acetone, mp 124-126°. uv max (ethanol):
233, 319 nm (ε 13200, 3600). Sol in polar
organic solvents.Derivative
Diacetate.
C
19H
24O
5; mol wt 332.39.
C 68.66%, H 7.28%, O 24.07%.
Properties
Crystals from petr ether, mp 99-100°. uv max (ethanol):
227, 313 nm (ε 12900, 3400).