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Download fileEnantioselective Total Synthesis of (+)-Euphorikanin A
journal contribution
posted on 2021-05-27, 21:44 authored by Moritz
J. Classen, Markus N. A. Böcker, Remo Roth, Willi M. Amberg, Erick M. CarreiraWe 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.