13-01719. Caldariomycin [Archived]
Nomenclature
CAS number: 465-61-2
(1S-trans)-2,2-Dichloro-1,3-cyclopentanediol; 1,3-dihydroxy-2,2-dichlorocyclopentane. C5H8Cl2O2; mol wt 171.02.
C 35.11%, H 4.71%, Cl 41.46%, O 18.71%.
Description and references
Mold metabolite from Caldariomyces fumago Woronichin. Isoln and structure: Clutterbuck et al., Biochem. J. 34, 664 (1940). Biosynthesis: Shaw et al., J. Biol. Chem. 234, 2560 (1959); Beckwith, ibid. 238, 3086 (1963); Beckwith, Hager, ibid. 3091. Synthesis: eidem, J. Org. Chem. 26, 5206 (1961); Burgstahler et al., ibid. 31, 3516 (1966). Abs configuration: Johnson et al., J. Am. Chem. Soc. 90, 136 (1968).
Properties
Fine, colorless needles, mp 121°. Decomposes at temps >180°; very stable to heat at mod. temps. [α]205461 +59.2° (c = 0.338 in H2O). Readily sol in cold water, ethanol, ether and most other org solvents. Slightly sol in chloroform.Status
This monograph has been retired and is no longer subject to revision or update.