Integrated synthesis of 3,4-carbazoquinone alkaloids N-Me-carbazoquinocin A, B and D–F

Abstract

Carbazole alkaloids carbazoquinocin A–F possessing a 1-alkyl-2-methyl-3,4-ortho-carabazoquinone framework were isolated from the microorganism Streptomyces violaceus 2448-SVT2 in 1995. Furthermore, they were found to exhibit strong inhibitory activity against lipid peroxidation. Herein, we report the integrated synthesis of N-Me-analogues of 5 members of the carbazoquinocin family of natural products, namely, N-Me-carbazoquinocin A, B and D–F. We employed an acid-catalyzed, intramolecular benzannulation of indole-appended Z-enoate propargylic alcohols, which was developed earlier in our laboratory, for the construction of the required carbazole framework. All five natural products were obtained in an overall yield of 50–60%, starting from a commercially available indole.