(Z)-2-Methyl-2-butenoic acid [(1S,2R,7aR)-hexahydro-2β-hydroxy-1H-pyrrolizin-1β-yl]methyl ester

Description

A pyrrolizidine alkaloid, macrophylline has been isolated from Senecio amphibolus and S. macrophylla MB. It forms a low melting solid which has not yet been obtained in a crystalline form. The base is dextrorotatory having a specific rotation of [α]²⁰_D + 34.52° (c 1.68, EtOH). When hydrolyzed with dilute acids the base furnishes macronecine and angelic acid. It has been characterized as the crystalline bitartrate which melts at 162-4°C.

Definition

ChEBI: Macrophylline is a member of pyrrolizines.

References

Danilova et al.,J. Gen. Chem. USSR, 23,1417 (1953)
Danilova, Kuzovkov, ibid, 23,1597 (1953)
Danilova, Utkin, Massagetov, ibid, 25, 797 (1955)
Danilova, Utkin, ibid, 30, 345 (1960)
Culvenor, Geissman,J. Org. Chem., 26, 3045 (1961)