Title: Hirsutic Acid C
CAS Registry Number: 3650-17-7
CAS Name: (1aR,2R,3aR,3bR,5S,6aR,7aS)-Decahydro-2-hydroxy-3a,5-dimethyl-3-methylenecyclopenta[4,5]pentaleno[1,6a-b]oxirene-5-carboxylic acid
Additional Names: 6b,6ab-epoxy-2,3,3aa,3b,4,5,6,6a,7,7aa-decahydro-5b-hydroxy-2b,3bb-dimethyl-4-methylene-1H-cyclopenta[a]pentalene-2-carboxylic acid
Molecular Formula: C15H20O4
Molecular Weight: 264.32
Percent Composition: C 68.16%, H 7.63%, O 24.21%
Literature References: Antibiotic metabolite isolated from the fungus Stereum hirsutum: Heatley et al., Br. J. Exp. Pathol. 28, 35 (1947). Structure and stereochemistry: Comer et al., Chem. Commun. 1965, 310; Comer, Trotter, J. Chem. Soc. B 1966, 11; Comer et al., Tetrahedron 23, 4761 (1967). Synthesis of (±)-form: Hashimoto et al., Tetrahedron Lett. 1974, 3745; M. Yamazaki et al., Chem. Lett. 1981, 1245. Stereosynthesis: B. M. Trost et al., J. Am. Chem. Soc. 101, 1284 (1979); of (+)-form: M. Shibasaki et al., Tetrahedron Lett. 23, 5311 (1982).
Properties: Prisms from ethanol, mp 179-182°. [a]D23 +116° (c = 1.05).
Melting point: mp 179-182°
Optical Rotation: [a]D23 +116° (c = 1.05)
Derivative Type: Methyl ester
Molecular Formula: C16H22O4
Molecular Weight: 278.34
Percent Composition: C 69.04%, H 7.97%, O 22.99%
Properties: Colorless prisms, mp 161-162°. [a]D20 +119° (c = 2.25).
Melting point: mp 161-162°
Optical Rotation: [a]D20 +119° (c = 2.25)
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