Application d'un schéma biogénétique en synthèse totale: L'ellipticine

Fischer indole synthesis applied to the total synthesis of natural products

“…The latter afforded the corresponding natural product ellipticine 16 in several reaction steps. 65 A series of 11-alkylbenzo[a]carbazole derivatives 22 and their dihydro analogues have been prepared and examined for their binding attraction for the estrogen receptor and their antiestrogenic and estrogenic effects in the immature mouse. They also showed mammary tumor inhibiting property.…”

Biomimetic Synthesis of Alkaloids Derived from Tryptophan: Indolemonoterpene Alkaloids

“…For instance, the key step of the pioneering biomimetic synthesis of ellipticine (57) by Langlois et al [34] (Scheme 3.13) involves cyclization of the imminium 58, followed by oxidation, according to the biogenetic hypothesis previously published by Potier and Janot, which involves fragmentation of the C5-C6 bond of the Corynanthe alkaloid stemmadenine (59) followed by rearrangement [35] (Scheme 3.14). …”