The rich variety of functionality and skeleton among the thousands of indole alkaloids, combined with their pharmacological properties, has long intrigued and challenged generations of chemists, for both structure elucidation and synthesis. Eventually, all were found to have a common biogenetic origin from a single universal precursor, the glucoalkaloid strictosidine, formed by condensation of tryptamine with the monoterpenoid glucoside secologanin. Most indole alkaloids contain two structural elements: tryptamine and a C-9/C-10 unit derived from secologanin. They are classified into three basic structural types according to the arrangement of the C-9/C-10 skeleton to form the Corynanthe, Aspidosperma and Iboga types, typified by ajmalicine, vindoline and catharanthine, respectively. Ever since secologanin become available in large quantities, it has been exploited as the starting material in enantiospecific alkaloid synthesis for more than three decades. In general, the approach has been " biomimetic", following the key steps according to the similar mechanism that occur in nature (biosynthesis) or which are thought to occur (biogenesis); the term "biogenetic-type synthesis" is also used. It also could contribute to elucidation of some aspects of the biosynthesis of these alkaloids, as well as providing a means of obtaining large quantities for pharmacological purposes of those only isolated in minor amounts. This review focuses on biogenetic-pattemed syntheses of monoterpenoid indole alkaloids from secologanin and its derivatives, for example, heteroyohimbines, yohimbines, oxindole alkaloids, antirhine and its derivatives, aspidosperma alkaloid analogs, cadambine and camptothecin.

Key words: MONOTERPENES, INDOLE P, ALKALOID, BIOSYNTHESIS