13-04646. Helminthosporal [Archived]
Nomenclature
CAS number: 723-61-5
(1R,4R,5S,8S)-1,7-Dimethyl-4-(1-methylethyl)bicyclo[3.2.1]oct-6-ene-6,8-dicarboxaldehyde. C15H22O2; mol wt 234.33.
C 76.88%, H 9.46%, O 13.66%.
Description and references
Toxin produced as ()-form by the fungus Bipolaris sarokiniana Shoemaker (Helminthosporium sativum). Isoln: deMayo et al., Can. J. Chem. 39, 1608 (1961). Structure: deMayo et al., J. Am. Chem. Soc. 84, 494 (1962). Stereochemistry: deMayo et al., Can. J. Chem. 41, 2996 (1963). Total synthesis and absolute configuration: Corey, Nozoe, J. Am. Chem. Soc. 87, 5728 (1965); (+)-form: E. Piers, H. P. Isenring, Can. J. Chem. 55, 1039 (1977); of (±)-form: M. Yanagiya et al., Tetrahedron Lett. 1979, 1761.
Properties
Crystals from light petr, mp 56-59°. [α]D 49° (c = 1.18 in CHCl3). bp0.015 115-120°. uv max (ethanol): 266 nm (ε 11000).Derivative
Bis-oxime.C15H24N2O2; mol wt 264.36.
C 68.15%, H 9.15%, N 10.60%, O 12.10%.
Properties
Crystals from alc, mp 177-182°.Status
This monograph has been retired and is no longer subject to revision or update.