Synthesis of a hybrid analog of the esperamicin and dynemicin cores

Add time:08/15/2019    Source:sciencedirect.com

An enediyne analog (2, R=H) that is a hybrid of the core structures of esperamicin and dynemicin was prepared. The key step in its synthesis was a Reissert-type reaction that involved intramolecular addition of the anion of a Z-1,3-diyn-2-ene to an N-acyl tetrahydrophenathridinium intermediate. It was found that 2 (R=H) readily undergoes epoxide rearrangement to an allylic alcohol (16). Both 2 (R=H) and 16 form the same cycloaromatized product 17 when heated in MeOH at 45 °C.

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