Issue 41, 2016

A diversity-oriented approach to indolocarbazoles via Fischer indolization and olefin metathesis: total synthesis of tjipanazole D and I

Abstract

New synthetic strategies to indolocarbazoles have been reported via two-fold Fischer indolization under green conditions using L-(+)-tartaric acid and N,N-dimethyl urea. Starting with cyclohexanone, a bench-top starting material, this methodology has been extended to the total synthesis of natural products such as tjipanazoles D and I as well as the core structure of asteropusazole and racemosin B. Here, atom economical reactions like ring-closing metathesis, enyne-metathesis, and the Diels–Alder reaction have been used as key steps. Diverse strategies demonstrated here are useful in medicinal chemistry and materials science to design a library of decorated indoles.

Graphical abstract: A diversity-oriented approach to indolocarbazoles via Fischer indolization and olefin metathesis: total synthesis of tjipanazole D and I

Supplementary files

Article information

Article type
Paper
Submitted
04 Aug 2016
Accepted
16 Sep 2016
First published
16 Sep 2016

Org. Biomol. Chem., 2016,14, 9868-9873

A diversity-oriented approach to indolocarbazoles via Fischer indolization and olefin metathesis: total synthesis of tjipanazole D and I

S. Kotha, M. Saifuddin and V. R. Aswar, Org. Biomol. Chem., 2016, 14, 9868 DOI: 10.1039/C6OB01679K

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