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

Cominetti, Marco M. D., Goddard, Zoë R. ORCID:, Hood, Bethany R., Beekman, Andrew M. ORCID:, O'Connell, Maria A. ORCID: and Searcey, Mark ORCID: (2024) Borylation via iridium catalysed C–H activation: a new concise route to duocarmycin derivatives. Organic & Biomolecular Chemistry, 22 (27). pp. 5603-5607. ISSN 1477-0520

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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.

Item Type: Article
Additional Information: Data availability: The data supporting this article have been included as part of the ESI. Funding information: EPSRC for funding support (EP/S026563). Dr Rianne Lord for use of glovebox facilities. Mr Anthony Hinchcliffe for HR-MS and BBSRC for equipment funding (BB/T017708/1).
Uncontrolled Keywords: duocarmycin,synthesis,dna alkylation,c-h activation,2* ,/dk/atira/pure/researchoutput/REFrank/2_
Faculty \ School: Faculty of Science > School of Pharmacy
Faculty of Science > School of Chemistry
Faculty of Science
UEA Research Groups: Faculty of Medicine and Health Sciences > Research Centres > Norwich Institute for Healthy Aging
Depositing User: LivePure Connector
Date Deposited: 21 Jun 2024 14:30
Last Modified: 10 Jul 2024 16:31
DOI: 10.1039/d4ob00814f


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