The alkaloids of the ervatamine-silicine group constitute a group of 2-acylindole alkaloids of the Corynanthean type, with an unusual skeleton, in which the carbon atoms of the tryptamine fragment (C5-C6) are in a rearranged situation, forming C5-C16 and C6-C16 bonds.The stereocontrolled assembling of the tetracyclic skeleton of ervatamine-silicine alkaloids wasplanned in three key steps: i) stereoselective conjugate addition of an organocuprate to an unsaturated bicyclic lactam, ii) stereoselective alkylation, and iii) closure of the carbocyclic ring by ring-closing olefin metathesis. The subsequent removal of the chiral auxiliary and the adjustment of the oxidation level completed the first total enantioselective synthesis of 16-episilicine.

Enantioselective synthesis of indole alkaloids of the ervatamine-silicine group

240th National Meeting (2010)

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