THESIS
2015
xiii, 122 pages : illustrations ; 30 cm
Abstract
In connection with the total synthesis of a marine macrolide, amphidinolactone B, this thesis deals with the synthesis of the C8–C12 fragment of this molecule.
In the first chapter, a brief overview on amphidinolactone B is introduced, including structural information, bioactivity, and synthetic work reported on related amphidinolide B, D, H, G, and L. As a key tactic for the construction of chirality in this synthesis, the well-developed asymmetric alkylation of the 4-substituted γ-butyrolactones is discussed in particular. This is followed by the retrosynthetic analysis and synthetic plan of the C8–C12 fragment.
Chapter 2 mainly covers the synthetic routes and results. First, an attempt on an olefination strategy was examined with failure in the formation of C8–C9 alkene...[
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In connection with the total synthesis of a marine macrolide, amphidinolactone B, this thesis deals with the synthesis of the C8–C12 fragment of this molecule.
In the first chapter, a brief overview on amphidinolactone B is introduced, including structural information, bioactivity, and synthetic work reported on related amphidinolide B, D, H, G, and L. As a key tactic for the construction of chirality in this synthesis, the well-developed asymmetric alkylation of the 4-substituted γ-butyrolactones is discussed in particular. This is followed by the retrosynthetic analysis and synthetic plan of the C8–C12 fragment.
Chapter 2 mainly covers the synthetic routes and results. First, an attempt on an olefination strategy was examined with failure in the formation of C8–C9 alkene functionality. Then, an 11-step sequence staring from L-glutamic acid was established to access the desired C8–C12 fragment of amphidinolactone B. Highlighted in the sequence of reactions are the substrate-controlled asymmetric alkylation of γ-butyrolactones, chemoselective tosylation/mesylation reaction of the triol, and epoxide ring-opening reaction with the sulfur ylide.
The experimental procedures and compound characterization data are provided in the experimental section. Copies of selected
1H and
13C NMR spectra are presented in Appendix.
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