Borylation iridium catalysed C-H activation: a new concise route to duocarmycin derivatives

The synthesis of the ethyl ester analogue of the ultrapotent antitumour antibiotic seco-duocarmycin SA has been achieved in eleven linear steps from commercially available starting materials. The DSA alkylation subunit can be made in ten linear steps from the same precursor. The route involves C-H a...

Full description

Saved in:
Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 22; no. 27; pp. 563 - 567
Main Authors Cominetti, Marco M. D, Goddard, Zoë R, Hood, Bethany R, Beekman, Andrew M, O'Connell, Maria A, Searcey, Mark
Format Journal Article
Published 10.07.2024
Online AccessGet full text

Cover

More Information
Summary:The synthesis of the ethyl ester analogue of the ultrapotent antitumour antibiotic seco-duocarmycin SA has been achieved in eleven linear steps from commercially available starting materials. The DSA alkylation subunit can be made in ten linear steps from the same precursor. The route involves C-H activation at the equivalent of the C7 position on indole leading to a borylated intermediate 9 that is stable enough for peptide coupling reactions but can be easily converted to the free hydroxyl analogue. A concise synthesis of an alkylation subunit of the duocarmycins is achieved via a C-H-activation approach. The ethyl ester analogue of duocarmycin SA can be made in eleven linear steps from a commercially available precursor.
Bibliography:https://doi.org/10.1039/d4ob00814f
Electronic supplementary information (ESI) available. See DOI
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00814f