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

ABSTRACT: 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.

SUBMITTER: Cominetti MMD

PROVIDER: S-EPMC11234497 | biostudies-literature | 2024 Jul

REPOSITORIES: biostudies-literature

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Borylation <i>via</i> iridium catalysed C-H activation: a new concise route to duocarmycin derivatives.

Cominetti Marco M D MMD Goddard Zoë R ZR Hood Bethany R BR Beekman Andrew M AM O'Connell Maria A MA Searcey Mark M

Organic & biomolecular chemistry 20240710 27

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 ana ...[more]

PMID: 38904084

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