7535. Pleurotin(e)

Nomenclature

CAS number: 1404-23-5
(2aα,4aβ,5β,6β,8aα,12bβ,12cβ,12dβ)-(-)-2a,3,4,4a,5,6,7,8a,12b,12c-Decahydro-6-methyl-2H-5,12d-ethanofuro[4′,3′,2′:4,10]anthra[9,1-bc]oxepin-2,9,12-trione.
C21H22O5; mol wt 354.40.
C 71.17%, H 6.26%, O 22.57%.

Description and references

Antibiotic substance produced by the fungus Pleurotus griseus: Robbins et al., Bull. Torrey Bot. Club 72, 165 (1945). Isoln: Robbins et al., Proc. Natl. Acad. Sci. USA 33, 171 (1947). Partial structure: Huls, Publ. Univ. Congo Elisabethville 4, 109 (1962), C.A. 3894f (1965). Structure and stereochemistry: J. Grandjean, R. Huls, Tetrahedron Lett. 1974, 1893. Synthesis of racemate: D. J. Hart, H.-C. Huang, J. Am. Chem. Soc. 110, 1634 (1988).

Chemical structure

Properties

Amber crystals from ether + chloroform, mp 200-215°. [α]D23 -20° (chloroform). Neutral reaction. Sparingly sol in water which inactivates it. More stable at acid pH, but still loses ≈50% of its activity when boiled for 10 min at pH 3. Aq solns also are inactivated on exposure to light. Moderately sol in alcohol, ether. Freely sol in chloroform.