Abstract
An efficient total synthesis of aperidine was accomplished using a Rh-catalyzed C-H insertion of a cis-dihydrobenzofuran ring. To circumvent the facile epimerization of the cis-dihydrobenzofuran ring, we designed and prepared the C-H insertion precursor diazoamide by Raines' protocol. Finally, the efficient incorporation of a guanidine group and mild deprotection conditions yielded this labile natural product.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Beer
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Benzofurans / chemical synthesis*
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Benzofurans / chemistry
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Benzofurans / pharmacology
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Catalysis
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Guanidines / chemical synthesis*
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Guanidines / chemistry
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Guanidines / pharmacology
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Molecular Structure
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Muscarinic Antagonists / chemical synthesis*
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Muscarinic Antagonists / chemistry
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Muscarinic Antagonists / pharmacology
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Rhodium / chemistry
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Stereoisomerism
Substances
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Benzofurans
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Guanidines
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Muscarinic Antagonists
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aperidine
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Rhodium