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Classen, Moritz J; Böcker, Markus N. A; Roth, Remo; Amberg, Willi M; Carreira, Erick M
Journal of the American Chemical Society, 06/2021, Letnik: 143, Številka: 22Journal Article
We disclose the first total synthesis of (+)-euphorikanin A, an ingenane-derived natural product featuring an unprecedented 5/6/7/3-fused tetracyclic skeleton. Key to the approach is a SmI2-mediated ketyl–enoate reaction that leads to the formation of two rings in a single step. The polarity-reversed cyclization proceeds in excellent yield and high diastereoselectivity. Access to ring B is effected late in the synthesis by implementation of a number of chemoselective transformations, including in situ generation of a vinyl lithium species and subsequent intramolecular attack onto an α-ketolactone.
