Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades
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Jamison_Total synthesis.pdf
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Author(s)
Underwood, Brian Saxton
Tanuwidjaja, Jessica
Ng, SzeSze
Jamison, Timothy F
Date Issued
April 2013
Journal
Tetrahedron
Publisher
Elsevier
Citation
Underwood, Brian S.; Tanuwidjaja, Jessica; Ng, Sze-Sze and Jamison, Timothy F. "Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades." Tetrahedron 69, 25 (June 2013): 5205-5220 © 2013 Elsevier Ltd
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Author's final manuscript
Abstract
Herein we describe in full our investigations leading to the first total syntheses of ent-dioxepandehydrothyrsiferol and armatol A. Discovery of a bromonium-initiated epoxide-opening cascade enabled novel tactics for constructing key fragments found in both natural products and have led us to revise the proposed biogeneses. Other common features found in the routes include convergent fragment coupling strategies to assemble the natural products' backbones and the use of epoxide-opening cascades for rapid constructions of the fused polyether subunits. Through de novo synthesis of armatol A, we elucidate the absolute and relative configuration of this natural product.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-NonCommercial-NoDerivs License
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DOI of Published Version
https://doi.org/10.1016/j.tet.2013.04.041
