Abstract
Enantiopure alpha,beta-unsaturated delta-lactams 1 and 2 react stereoselectively with carbon-, nitrogen-, sulfur-, and oxygen-centered nucleophiles. The synthetic potential of these conjugate additions is demonstrated through the synthesis of two new substituted indolizidines: (7R)-7-amino-8-deoxyswainsonine 3 and (7R)-7-acetylaminoswainsonine 4.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Carbon / chemistry*
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Hydroxylation
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Indolizines / chemistry*
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Molecular Structure
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Nitrogen / chemistry*
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Oxygen / chemistry*
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Stereoisomerism
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Sulfur / chemistry*
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Swainsonine / analogs & derivatives
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Swainsonine / chemical synthesis
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Swainsonine / chemistry*
Substances
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6,7-dehydro-5-oxoindolizidine
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Indolizines
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Sulfur
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Carbon
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Nitrogen
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Swainsonine
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Oxygen