Abstract
[reaction: see text] Total synthesis of hyacinthacine A(1) and its epimer at C3 is described. The synthesis includes a stereocontrolled carboazidation of a chiral allylsilane as a key step. C-Si bond oxidation and reduction of the azide, with ring-closure, complete the total synthesis, which establishes the absolute configuration of 3.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Cyclization
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Enzyme Inhibitors / chemical synthesis
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Enzyme Inhibitors / chemistry
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Glycoside Hydrolases / antagonists & inhibitors
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Liliaceae / chemistry
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Molecular Structure
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Oxidation-Reduction
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Plants, Medicinal / chemistry
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Pyrrolizidine Alkaloids / chemical synthesis*
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Pyrrolizidine Alkaloids / chemistry
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Stereoisomerism
Substances
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Enzyme Inhibitors
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Pyrrolizidine Alkaloids
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hyacinthacine A1
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Glycoside Hydrolases