(1S)-2',3',8',8'aβ-Tetrahydro-5'-hydroxy-6'-methoxy-1'-methylspiro[2-cyclohexene-1,7'(1'H)-cyclopent[ij]isoquinolin]-4-one

The empirical formula for this alkaloid from Croton linearis Jacq. was originally given as C 1 7H 1903N, representing it as a dihydrocrotonosine. This was later altered to that given above when it was shown that a methylimino group is present. The structure has now been confirmed as dihydro-N-methylcrotonosine. When crystallized from EtOH it forms anisotropic columns. The ultraviolet spectrum shows three absorption maxima at 228, 282 and 288 ffi/J. and the specific rotation in [o:Jf>8 + 116° (c 0.83, MeOH). The hydrochloride also forms colourless columnar crystals which decompose, without melting, above 300°C. One phenolic hydroxyl group is present and on methylation, the alkaloid yields Amuronine (q.v.).

Haynes, Stuart.,J. Chem. Soc., 1784, 1789 (1963)
Haynes etaZ., Proc. Chem. Soc., 261 (1964)
Haynes et aZ., J. Chem. Soc., C, 1676 (1966)
Structure:
Snatzke, Wollenberg.,J. Chem. Soc., C, 1681 (1966)