Synthesis of the Guaianolide Ring System via Cycloaddition of a Bicyclic Carbonyl Ylide with Allyl Propiolate

Synthesis of the Guaianolide Ring System via Cycloaddition of a Bicyclic Carbonyl Ylide with Allyl Propiolate

A cyclic carbonyl ylide with a trans-annulated cyclopentane ring was generated by a Rh2(OAc)4-catalyzed reaction from a diazoketone precursor and trapped with allyl propiolate. The 1,3-dipolar cycloaddition led to the stereoselective formation of an oxygen-bridged polycycle. Via Curtius degradation,...

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Veröffentlicht in:Organic letters 2010-08, Vol.12 (15), p.3418-3421
Hauptverfasser: Navickas, Vaidotas, Ushakov, Dmitry B, Maier, Martin E, Ströbele, Markus, Meyer, H.-Jürgen
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Cyclization
Cyclopentanes - chemistry
Molecular Structure
Rhodium - chemistry
Sesquiterpenes, Guaiane - chemical synthesis
Sesquiterpenes, Guaiane - chemistry
Stereoisomerism
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Zusammenfassung:A cyclic carbonyl ylide with a trans-annulated cyclopentane ring was generated by a Rh2(OAc)4-catalyzed reaction from a diazoketone precursor and trapped with allyl propiolate. The 1,3-dipolar cycloaddition led to the stereoselective formation of an oxygen-bridged polycycle. Via Curtius degradation, the cycloadduct was transformed to the ring skeleton typical of the sesquiterpene family of guaianolides.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1012185