Abstract
A stereoselective synthesis of the BCDE fragment of brevetoxin A has been completed. anti-Glycolate aldol, glycolate alkylation, and ring-closing metathesis reactions were employed as key bond-forming events. A convergent assembly strategy was employed that relied on a Horner-Wadsworth-Emmons union of two complex fragments. Subsequent cyclization and dehydration led to efficient generation of an intermediate endocyclic enol ether, which was advanced to a tetracyclic fragment. [reaction: see text]
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Alkylation
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Catalysis
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Cyclization
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Ethers, Cyclic / chemical synthesis*
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Ethers, Cyclic / chemistry
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Marine Toxins / chemical synthesis*
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Marine Toxins / chemistry
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Molecular Structure
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Oxocins / chemical synthesis*
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Oxocins / chemistry
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Polycyclic Aromatic Hydrocarbons / chemical synthesis*
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Polycyclic Aromatic Hydrocarbons / chemistry
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Stereoisomerism
Substances
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Ethers, Cyclic
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Marine Toxins
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Oxocins
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Polycyclic Aromatic Hydrocarbons
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Brevetoxin A