4899. Illudins

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).

Chemical structure

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′-[5H]inden]-7′(6′H)-one.
C15H20O3; 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

Monoacetate.
C17H22O4; mol wt 290.35.
C 70.32%, H 7.64%, O 22.04%.

Properties

mp 75-76° from petr ether.

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′-[5H]inden]-7′(6′H)-one; lampterol; lunamycin (obsolete).
C15H20O4; 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.
C19H24O5; 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).