6533b7d2fe1ef96bd125f6ad

RESEARCH PRODUCT

A Modular Access to (±)-Tubocurine and (±)-Curine - Formal Total Synthesis of Tubocurarine.

Dorota FerencTill OpatzNicola Otto

subject

Molecular Structure010405 organic chemistryStereochemistryChemistryAlkaloidOrganic ChemistryCurare alkaloidsChemistry OrganicTotal synthesisTubocurarine010402 general chemistryIsoquinolines01 natural sciencesCatalysis0104 chemical sciencesTubocurineBenzaldehydesCopper

description

Two consecutive Cu-catalyzed Ullmann-type C–O couplings permitted the first successful entry toward the curare alkaloids (±)-tubocurine and (±)-curine. Starting from vanillin, the synthetic sequence comprises 15 linear steps and includes a total of 24 transformations. In addition, the total synthesis of tubocurine represents a formal total synthesis of the famous arrow poison alkaloid tubocurarine.

10.1021/acs.joc.6b02647https://pubmed.ncbi.nlm.nih.gov/27997804