A possible biosynthetic relationship between the cyclopentanoid monoterpenes and the indole alkaloids

✍ Scribed by R. Thomas

• Publisher: Elsevier Science
• Year: 1961
• Tongue: French
• Weight: 466 KB
• Volume: 2
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)91645-4

✦ Synopsis

IN the well-known Barger-Hahn hypothesis 192 the carbon skeleton of yohimbine (I), is considered to be derived from tryptamine, phenylalanine and formaldehyde or its Cl equivalent. This proposal later gained considerable support as a consequence of the attractive suggestion of Woodward, 3 that a related pathway involving the fission of a j,&dihydro~henylalsnine-derived ring E with the incorporation of a single acetate unit, could simply explain the origin of strychnine. A most valuable consequence of this novel postulate has been the susoessful biosynthetic anticipation of the subsequently determined structures of a number of other indole alkaloids of varying degrees of complexity, e.g. corynsntheine (II)4 and echitamine (III),5 and also the isoquinoline base, emetine (IV).6 Although in relation to the indole alkaloids the utilization of a tryptamine unit is almost self-evident and has indeed recently been demonstrated