Issue 30, 2023

Total synthesis of atropisomeric indolosesquiterpenoids via N–N bond formation: dixiamycins A and B

Abstract

N–N dimeric indolosesquiterpene alkaloids constitute a class of under-investigated architecturally intriguing natural products. Herein, we report the first chemical oxidation approach to the asymmetric total syntheses of these atropisomeric indolosesquiterpenoids through N–N bond formation. Specifically, dixiamycins A (1a) and B (1b) were prepared through a Cu(I)-mediated aerobic dehydrogenative dimerization from the naturally occurring monomer xiamycin A methyl ester (2b); this preparation also represents the first total synthesis of dixiamycin A (1a). The monomer xiamycin A methyl ester (2b) was synthesized via a late-stage Buchwald Pd(II)-mediated aerobic dehydrogenative C–N bond formation.

Graphical abstract: Total synthesis of atropisomeric indolosesquiterpenoids via N–N bond formation: dixiamycins A and B

Supplementary files

Article information

Article type
Edge Article
Submitted
30 dek 2022
Accepted
17 iyn 2023
First published
20 iyn 2023
This article is Open Access

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

Chem. Sci., 2023,14, 8047-8053

Total synthesis of atropisomeric indolosesquiterpenoids via N–N bond formation: dixiamycins A and B

R. Nandi, S. Niyogi, S. Kundu, V. R. Gavit, M. Munda, R. Murmu and A. Bisai, Chem. Sci., 2023, 14, 8047 DOI: 10.1039/D2SC07119C

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