Strategies, Setbacks, and Successes in the Synthesis of (-)-Spiroleucettadine

The Journal of Organic Chemistry
Richard A LambBill C Hawkins

Abstract

Various strategies toward the synthesis of the marine natural product (-)-spiroleucettadine are described. In the original strategy, a biomimetic inspired oxidation of a 2-imidazoline scaffold uncovered unexpected reactivity, where benzylic oxidation followed by a Baeyer-Villiger reaction was observed. The second generation approach examined oxidative dearomatization of the phenol ring system first, where a competing spirocyclization process was uncovered. Efforts to forge the scaffold via a carbocation mediated benzyl migration were unsuccessful. Highlights of the successful synthesis include two consecutive hypervalent iodine reactions: the first formed the spirocyclic center and the second facilitated installation of an acetate group at the C-5 position to allow for subsequent introduction of the methyl amine side chain.

References

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Citations

Dec 16, 2020·ChemMedChem·Michael P BadartBill C Hawkins
Jan 26, 2021·The Journal of Organic Chemistry·Satish G MoreGurunath Suryavanshi

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