Himeradine A : synthetic efforts towards himeradine A and related natural products, a Michael reaction focused approach Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/xk81jn99d

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  • Lycopodium alkaloids have generated enormous amounts of interest from the scientific community, both as synthetic targets and for their medicinal properties. Herein is described work towards a unifying approach to large segments of the Lycopodium family. An organocatalyzed intramolecular heteroatom Michael reaction method, for the construction of piperidine and piperizine rings has been developed. The method, described herein, has been utilized in the construction of pelletierine and homopipecolic acid. An initial route to the C₁٫-C₁₁٫ quinolizidine fragment of himeradine A utilized a scope expanded version of our heteroatom Michael method to construct the C₁₀٫-N₁٫ ring. The C₁٫-C₁₀٫ quinolizidine portion was synthesized by intramolecular amide alkylation. Numerous routes were explored for the formation of the C₁₀٫-C₁₁٫ bond. A second generation route to the C₁٫-C₁₁٫ quinolizidine fragment of himeradine A was developed. The C₁₀٫-N₁٫ ring was formed by Lewis acid-catalyzed diastereocontrolled intramolecular Michael reaction. The C₆٫-C₂٫ ring was formed by Wittig reaction and subsequent lactam bond formation. A model system for the installation of the C₁₇-C₁₅ portion of himeradine A containing the stereodefined N₁₈ was demonstrated. With a viable synthesis of C₁٫-C₁₁٫ quinolizidine fragment, the C₁-C₁₇ fragment was developed. Several routes were explored for the functionalization of the C₁-C₁₄ fragment, a Mander's reagent strategy successfully installed C₁₅. A modified approach to the C₁٫-C₁₁٫ quinolizidine was explored. The C₁₇-C₁₆ portion was installed using a Wittig reaction. Potential coupling strategies with the C₁-C₁₅ fragment were developed.
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