Progress toward the total synthesis of the marine natural product amphidinol 3 Public Deposited

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Last Modified
  • March 21, 2019
Creator
  • Martin, Timothy James
    • Affiliation: College of Arts and Sciences, Department of Chemistry
Abstract
  • A convergent synthesis of the C31-C52 bis-tetrahydropyran core of the natural product amphidinol 3 is reported. A common intermediate was synthesized from D-tartaric acid utilizing an asymmetric glycolate alkylation/ring-closing metathesis sequence to construct the THP rings. Differential elaboration of the common intermediate allowed the synthesis of two distinct coupling partners, which were joined through a modified Horner-Wadsworth-Emmons olefination to provide the bis-tetrahydropyran core. A convergent approach to the C9-C29 fragment has also been achieved, utilizing Julia-Kocienski olefination to unite key fragments. Exploiting the repeating units of the C1-C17 domain of the polyol fragment, stereocenters C2, C6, C10, and C14 have all been introduced via the asymmetric glycolate alkylation reaction. An iterative acetate aldol sequence followed by a propionate aldol provided the carbon skeleton and required stereocenters of the C21-C29 domain. Following completion of the polyol domain, union with the bis-tetrahydropyran core is envisioned to introduce the C1-C52 domain of amphidinol 3.
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  • "... in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Department of Chemistry."
Advisor
  • Crimmins, Michael T.
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  • Chapel Hill, NC
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  • Open access
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