Dictyodendrin A is a marine alkaloid known to possess inhibitory activity against telomerase and is of interest for use as a potential target for cancer chemotherapy. A retro-synthetic route to Dictyodendrin A by sequential C�H functionalization reactions can be envisioned utilizing a combination of the Davies and Itami C-H functionalization methodologies. 1-substituted pyrroles can undergo selective C-H arylations at the 3-position with the use of a rhodium-(I) catalyst with p�accepting ligands. The regioselectivity of the carbenoid C-H functionalizations can be directed to the most sterically accessible C-H bonds of the pyrrole ring by using a bulky carbenoid compound containing a trichloroethyl ester moiety along with sterically encumbered Rh2(S-TCPTAD)4 catalyst.

Synthesis of dictyodendrin A via sequential C-H functionalizations

248th National Meeting (2014)

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