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Scholarly Works (2 results)

  • Thesis
  • Peer Reviewed
UCLA Electronic Theses and Dissertations (2021)

Chapter 1 presents an overview and classification of furan-containing natural products based on skeletal structures, characteristic functional group or by the number of carbons. It also contains a summary of traditional as well as frequently encountered modern synthetic methodologies developed for the preparation of the furan nucleus.

Chapter 2 presents the development and applications of the Michael–Heck methodology for the synthesis of polyalkyl furans and polyalkyl furan-containing natural products, including furanoterpenes, furan fatty acids (F-acids) and their derivatives. Mechanistic investigations are also discussed in this chapter.

Chapter 3 presents attempts to apply the vinylogous Michael–Heck reaction to the total synthesis of furanosesquiterpenes agassizin, pallescensin G and F as well as various furanoeremophilanes using both intramolecular and intermolecular routes.

    Cover page: Michael–Heck Approach Towards the Synthesis of Highly Functionalized Polyalkyl Furans and Application of the Vinylogous Michael–Heck Reaction Towards the Total Synthesis of Furanosesquiterpenes and Furanoeremophilanes
    • Article
    • Peer Reviewed
    UCLA Previously Published Works (2021)
    Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non-trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael-Heck approach, using sequential phosphine-palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.
      Cover page: Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis.
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