Enantioselective Formal Synthesis of (−)-Englerin A via a Rh-Catalyzed [4 + 3] Cycloaddition Reaction

Enantioselective Formal Synthesis of (−)-Englerin A via a Rh-Catalyzed [4 + 3] Cycloaddition Reaction

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 provi...

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Veröffentlicht in:Organic letters 2010-08, Vol.12 (16), p.3708-3711
Hauptverfasser: Xu, Jing, Caro-Diaz, Eduardo J. E, Theodorakis, Emmanuel A
Format: Artikel
Sprache:eng
Schlagworte:
Antineoplastic Agents, Phytogenic - chemical synthesis
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - pharmacology
Catalysis
Cyclization
Furans - chemistry
Molecular Structure
Rhodium - chemistry
Sesquiterpenes, Guaiane - chemical synthesis
Sesquiterpenes, Guaiane - chemistry
Sesquiterpenes, Guaiane - pharmacology
Stereoisomerism
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1015652