Title page for ETD etd-05032000-14150026
|Type of Document
||Stereochemical Control of Polyketides
through Asymmetric Aldol Reaction
||Master of Science
|Calter, Michael A.
|Kingston, David G. I.
|Wolfe, James F.
- Aldol Reaction
- Asymmetric Synthesis
|Date of Defense
Polyketides are a group of complex natural products that can inhibit the growth of
bacteria, viruses, fungi, and tumor cells. Most polyketides are very difficult to extract from
bacteria. Therefore, numerous syntheses of polyketide-related synthons have been
However, controlling the stereochemistry of the polyketide poses the most
challenging task for researchers. The aim of this report is to discuss control of the
stereochemistry of the polyketide-related synthons in asymmetric aldol reactions. Several
important methodologies for stereochemical control in the aldol reaction exist. The first
approach is to control the enolate geometry and the aldehyde (or ketone) geometry. The second approach is to use a chiral auxiliary and chiral ligands. The third approach is to use
a chiral catalyst, which is the most efficient method if the catalyst operates with complete
efficiency. Proposed transition states are also described to explain the resulting
stereochemistry of the aldol adduct.
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