Stereoselective Desymmetrization Methods In The Assembly Of Complex Natural Molecules (springer Theses)
by Robert.J Sharpe /
2016 / English / PDF
21.8 MB Download
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.
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.
