Total syntheses of naturally occurring antiviral indolosesquiterpene alkaloids, xiamycins C–F via Csp3–H functionalization

Abstract

Concise total syntheses of naturally occurring antiviral indolosesquiterpene alkaloids, xiamycin C (2a), D (2b), E (2c) and F (2d), have been achieved via a late-stage oxidative δ-Csp3–H functionalization of an advanced pentacyclic enone intermediate 8. This strategy takes advantage of ipso-nitration of naturally occurring abietane diterpenoids to synthesize o-bromo nitroarene derivative 11. A Suzuki–Miyaura coupling of 11 with phenylboronic acid followed by Cadogan's ring closure provided a modular approach to a carbazole ring required for a functionalized pentacyclic core of indolosesquiterpene alkaloids.

Graphical abstract: Total syntheses of naturally occurring antiviral indolosesquiterpene alkaloids, xiamycins C–F via Csp3–H functionalization

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Article information

Article type
Edge Article
Submitted
22 Jun 2022
Accepted
21 Sep 2022
First published
21 Sep 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022, Advance Article

Total syntheses of naturally occurring antiviral indolosesquiterpene alkaloids, xiamycins C–F via Csp3–H functionalization

M. Munda, R. Nandi, V. R. Gavit, S. Kundu, S. Niyogi and A. Bisai, Chem. Sci., 2022, Advance Article , DOI: 10.1039/D2SC03479D

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