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Heck Cyclization Strategy for Preparation of Erythrinan Alkaloids: Asymmetric Synthesis of Unnatural (−)-Erysotramidine from L‑Tartaric Acid

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journal contribution
posted on 06.02.2015, 00:00 by Danuta Mostowicz, Mirosław Dygas, Zbigniew Kałuża
With an imide derived from l-tartaric acid as the starting material, ent-erysotramidine was synthesized for the first time. The synthesis features the use of the enantiopure synthon, prepared in a set of highly stereoselective reactions, including N-acyliminium cyclization, dihydrofuranyl ring formation via silver-catalyzed intramolecular alcohol addition to acetylene, and vinyl ether catalytic hydrogen reduction. The crucial step of the synthesis, assembly of ring A, was achieved by using Heck cyclization of (Z)-iodoolefin.