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    Exploration of copper-catalyzed Grignard cross-coupling between 3-halo-4-alkoxybenzoates and bromoisoprenoids

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    LUTIN-UNDERGRADUATERESEARCHOPTIONTHESIS-2022.pdf (760.8Kb)
    Date
    2022-05
    Author
    Lutin, David J.
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    Abstract
    Allylic functionality, often taking the form of terpenes, is a mainstay of marine natural products. The aryl-allyl connection is particularly common, appearing in several product classes derived from Callophycus serratus, many of which exhibit promising initial biological activities. In pursuit of several total syntheses, which leverage a copper-catalyzed Grignard cross-coupling between a 3-halo-4-alkoxybenzoate and geranylgeranyl bromide, we explored the effects of alkoxybenzoate and halogen substitutions on the coupling. By scrutinizing the constraints and influences of these protecting groups on cross-coupling success, we lay out the potential for downstream deprotection chemistry. Here, we present the results of this investigation, along with a theoretical basis for the observations.
    URI
    http://hdl.handle.net/1853/66748
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    • School of Chemistry and Biochemistry Undergraduate Research Option Theses [51]
    • Undergraduate Research Option Theses [862]

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