Abstract
[reaction: see text] Starting from (-)-quinic acid an efficient synthesis of highly functionalized cis-alpha,beta-unsaturated ketone 3, an advanced precursor of branimycin, has been accomplished via two key step reactions: a ring closing metathesis reaction to prepare the cis-decalin system, and a highly stereoselective epoxidation reaction.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Epoxy Compounds / chemistry
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Ketones / chemistry
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Macrolides / chemical synthesis*
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Macrolides / chemistry
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Models, Molecular
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Molecular Structure
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Naphthalenes / chemical synthesis*
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Naphthalenes / chemistry
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Quinic Acid / chemistry*
Substances
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Epoxy Compounds
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Ketones
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Macrolides
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Naphthalenes
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branimycin
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Quinic Acid
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decalin