Abstract
[structure: see text] Michael addition of Me(2)Cu(CN)Li(2) to alpha,beta-unsaturated lactone 7 derived from beta-hydroxyl ketone 5 provides lactone 8, which is converted to alcohol 11 using Oppolzer's methodology as the key step. Connection of 11 with the l-proline moiety and subsequent installation of an oxazoline ring affords 16, which is coupled with tripeptide 21; subsequent macrocyclization then furnishes 4, an oxazoline analogue of apratoxin A.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents / chemical synthesis
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Cyclization
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Cytotoxins / chemical synthesis*
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Depsipeptides*
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Ketones / chemistry
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Lactones / chemical synthesis
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Models, Chemical
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Molecular Structure
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Oxazoles / chemical synthesis*
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Peptides / chemistry
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Peptides, Cyclic / chemical synthesis*
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Proline / chemistry
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Stereoisomerism
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Structure-Activity Relationship
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Thiazoles / chemistry
Substances
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Antineoplastic Agents
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Cytotoxins
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Depsipeptides
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Ketones
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Lactones
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Oxazoles
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Peptides
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Peptides, Cyclic
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Thiazoles
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apratoxin A
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Proline