Phosphate Tether-Mediated Metathesis Studies and Application Towards Natural Product Synthesis
Issue Date
2015-08-31Author
Maitra, Soma
Publisher
University of Kansas
Format
328 pages
Type
Dissertation
Degree Level
Ph.D.
Discipline
Chemistry
Rights
Copyright held by the author.
Metadata
Show full item recordAbstract
Over the past decade, work in our lab has focused on phosphate tether-mediated desymmetrization of C2-symmetric 1,3-anti-dienediol via ring-closing metathesis (RCM) to afford P-stereogenic bicyclo[4.3.1]phosphates. However, efforts in this direction relied solely on phosphate tether-mediated coupling of allylic alcohol cross partners with 1,3-anti-dienediol synthons leading to the formation of simple bicyclo[4.3.1]phosphates and their applications in natural product synthesis. The objective of this dissertation work is to advance the phosphate tether-mediated methods to include the construction of complex bicyclo[n.3.1]phosphates via ring-closing metathesis (RCM). The RCM study, discussed in detail in Chapter 2, highlights the synthetic potential of phosphates as a temporary tethers in facilitating the coupling of complex fragments to produce novel P-stereogenic bicyclic phosphate scaffolds. Chapter 3 describes the development of phosphate tether-mediated one-pot and two-pot sequential metathesis/reduction protocols towards the stereodivergent synthesis of complex polyols. The potential application of phosphate tether-mediated reactions en route to the synthesis of the C9–C25 fragment of spirastrellolide B is discussed in Chapter 4.
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- Chemistry Dissertations and Theses [335]
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