By R.H.F. Manske and R.G.A. Rodrigo (Eds.)
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Chasmanthum. The structure and stereochemistry of chasmaconitine (38)were assigned on the basis of the conversion of this alkaloid to delphinine. Chasmanthinine was also correlated with chasmaconitine and other alkaloids, and structure 39 was originally assigned to it. Thus far, neither of these two alkaloids has been isolated from any other plants. J. ISODELPHININE(BASE D) In 1959 Katsui and his co-workers (69, 70) isolated a diterpenoid alkaloid, designated initially as base D and later as isodelphinine, from the mother liquors accumulated during the isolation of miyaconitine and miyaconitinone from the roots of A.
This formula was also supported by Keller (49)and later by Markwood (50). In 1939 Jacobs and Craig (51) modified the molecular formula of delphinine to C33H45N09and assigned the nine oxygen atoms to four methoxyl groups, one hydroxyl group, one acetyl group, and a benzoyl group. In addition to this, they reported the presence of an N-methyl group in delphinine. The detailed chemistry of delphinine 12 S. WILLIAM PELLETIER AND NARESH V. MODY OH OH p““ CH,- OCH, OCH, OCH, 31 Delphinine 30 3 is covered in the last review article ( 3 )in this series.
C. DELPHATINE Delphatine (C26H43N07; mp 106") has been isolated from the seeds of D. biternatum (126, 127). Structure 147 was established for delphatine (18-0-methyllycoctonine) by chemical correlation with the well-known alkaloid lycoctonine (58). The only difference between these two alkaloids is that delphatine has a methoxyl group at C-18, while lycoctonine has a hydroxy group at that position.