2042. Chanoclavine

Nomenclature

CAS number: 2390-99-0
[4R-[4α,5β(E)]]-2-Methyl-3-[1,3,4,5-tetrahydro-4-(methylamino)benz[cd]indol-5-yl]-2-propen-1-ol; (E)-8,9-didehydro-6-methyl-6,7-secoergoline-8-methanol; chanoclavin-I; secaclavine.
C16H20N2O; mol wt 256.34.
C 74.97%, H 7.86%, N 10.93%, O 6.24%.

Description and references

Precursor of the tetracyclic ergolines, agroclavine, elymoclavine, and lysergic acid amide, q.q.v.: Gr"oger et al., Z. Naturforsch. 21b, 827 (1966); Floss et al., Chem. Commun. 1967, 105. Occurs in sclerotia of Claviceps purpurea (Fries) Tul., Hypocreaceae, in Ipomea tricolor Cav., Convolvulaceae and is one of the active principles of the ancient Aztec drug “Ololiuqui,” Rivea coryrubosa (L.) Hall. f., Convolvulaceae: Hofmann, Tscherter, Experientia 16, 414 (1960). Isoln and structure: Hofmann et al., Helv. Chim. Acta 40, 1358 (1957). Isoln of stereoisomers: Stauffacher, Tscherter, ibid. 47, 2186 (1964). Stereochemistry: Acklin et al., Chem. Commun. 1966, 799. Biosynthetic studies: Floss et al., J. Am. Chem. Soc. 90, 6500 (1968). Total synthesis of (±)-chanoclavine: H. Plieninger et al., Tetrahedron Lett. 1975, 1827; H. Plieninger, D. Schmalz, Ber. 109, 2140 (1976); M. Natsume, H. Muratake, Heterocycles 16, 375 (1981).

Chemical structure

Properties

Thick prisms and polyhedra from acetone or methanol, mp 220-222°. [α]D20 -240° (pyridine), [α]D20 -205° (c = 0.75 in alcohol). uv max: 225, 284, 293 nm (ε 4.44, 3.82, 3.72). One gram dissolves in 25 ml boiling methanol, 140 ml boiling acetone, 170 ml boiling ethyl acetate or 350 ml boiling chloroform. Practically insol in water.

Derivative

Epimer at position 10.

Nomenclature

Chanoclavine II.