Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades
Author(s)
Underwood, Brian Saxton; Tanuwidjaja, Jessica; Ng, SzeSze; Jamison, Timothy F
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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.
Date issued
2013-04Department
Massachusetts Institute of Technology. Department of ChemistryJournal
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
Version: Author's final manuscript
ISSN
0040-4020