Synthesis of indole analogues of the natural schweinfurthins.

ABSTRACT: An interest in the schweinfurthins, natural stilbenes with significant antiproliferative activity, has prompted efforts to prepare a set of indole analogues. To approach the desired compounds through a Horner-Wadsworth-Emmons condensation, new indole derivatives bearing a phosphonomethyl substituent in the B-ring were required. The parent indole system with the necessary substitution pattern was obtained through Stobbe condensation and cyclization. A prenyl substituent was incorporated at the C3 position of a 4,6-disubstituted indole through a highly regioselective electrophilic aromatic substitution reaction, while metalation and alkylation provided the C2-prenylated indole. After introduction of the phosphonate group through classical reactions, the new indole phosphonates were found to

SUBMITTER: Kodet JG 

PROVIDER: S-EPMC3940163 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature