Catalytic Asymmetric Aldol Equivalents for an Enantioselective Total Synthesis of Apoptolidin C
Apoptolidin C is a biologically active polypropionate macrolide isolated from the soil bacteria Nocardiopsis sp. The work presented herein highlights a novel approach to synthesizing the core of the natural product, apoptolidinone C, as well as a de-novo synthesis of the C9 sacharide. Our synthesis...
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| Format: | Dissertation |
| Language: | English |
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ProQuest Dissertations & Theses
01-01-2011
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| Online Access: | Get full text |
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| Summary: | Apoptolidin C is a biologically active polypropionate macrolide isolated from the soil bacteria Nocardiopsis sp. The work presented herein highlights a novel approach to synthesizing the core of the natural product, apoptolidinone C, as well as a de-novo synthesis of the C9 sacharide. Our synthesis utilizes a catalytic asymmetric approach to the construction of the complex polypropionate arrays contained in apoptolidin through the use of our acyl halide-aldehyde cyclocondensation (AAC) reaction. Employing the AAC technology using cinchona alkaloid derived catalysts, as well as the complementary chiral aluminum catalysts, we have successfully demonstrated a catalytic and asymmetric synthesis of the aglycone core of apoptolidin C. In addition, we have demonstrated the asymmetric synthesis of the C9 saccharide from achiral starting materials. |
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| ISBN: | 126723122X 9781267231222 |