Enantioselective Total Synthesis of (+)-Euphorikanin A
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Date
2021-06-09
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Journal Article
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Abstract
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.
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published
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143 (22)
Pages / Article No.
8261 - 8265
Publisher
American Chemical Society
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03511 - Carreira, Erick M. / Carreira, Erick M.