This thesis describes the inception, design, and implementation of
stereoselective desymmetrization reactions in the total synthesis
of the natural products pactamycin and paspaline. In the case of
pactamycin, the author develops a novel asymmetric Mannich reaction
and symmetry-breaking reduction strategy to enable facile
construction of the complex core architecture in fifteen steps
using commercially available materials - the shortest synthesis to
date. He subsequently demonstrates the flexibility of this approach
in SAR investigations by highlighting the preparation of
twenty-five unique pactamycin structural congeners. For paspaline,
the author develops a biocatalytic desymmetrization strategy that
allows the highly controlled synthesis of core stereochemistry and
provides a platform for the development of new conceptual
disconnections in the synthesis of "steroid-like" natural products.
This thesis offers a valuable resource for students embarking on a
PhD in total synthesis.
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