Abstract
An enantioselective formal synthesis of (-)-englerin A (1) is reported. Key to the strategy is a Rh-catalyzed [4 + 3] cycloaddition reaction between furan 10 and diazo ester 11 that, following an intramolecular aldol condensation, produces the tricyclic scaffold of englerin. This strategy also provides a rapid, efficient, and stereoselective access to the biologically significant core motif of the guaiane sesquiterpenes.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Antineoplastic Agents, Phytogenic / chemical synthesis*
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Antineoplastic Agents, Phytogenic / chemistry
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Antineoplastic Agents, Phytogenic / pharmacology
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Catalysis
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Cyclization
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Furans / chemistry*
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Molecular Structure
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Rhodium / chemistry*
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Sesquiterpenes, Guaiane / chemical synthesis*
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Sesquiterpenes, Guaiane / chemistry
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Sesquiterpenes, Guaiane / pharmacology
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Stereoisomerism
Substances
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Antineoplastic Agents, Phytogenic
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Furans
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Sesquiterpenes, Guaiane
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englerin A
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englerin B
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Rhodium