Biomimetic synthesis of dendridine A

Abstract

Biomimetic synthesis of the bisindole natural product dendridine A is reported. Although attempts to install the hindered biaryl bond by oxidative phenolic coupling of the 7-hydroxytryptamine 6 gave the undesired ortho-ortho product, a Scholl-type oxidative coupling of the 7-isopropoxytryptamine 9 with molybdenum pentachloride proceeded through the desired para-para pathway, installing the entire carbon framework of dendridine A.