Enantioselective Syntheses of Tremulenediol A and Tremulenolide A

Enantioselective Syntheses of Tremulenediol A and Tremulenolide A

An enantioselective entry to the skeleton of the tremulane sesquiterpenes is described. The approach features a series of efficient transition metal-catalyzed reactions commencing with an enantioselective rhodium(II)-catalyzed intramolecular cyclopropanation followed by a regioselective allylic alky...

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Veröffentlicht in:Organic letters 2005-09, Vol.7 (20), p.4535-4537
Hauptverfasser: Ashfeld, Brandon L, Martin, Stephen F
Format: Artikel
Sprache:eng
Schlagworte:
Alkylation
Carbon - chemistry
Lactones - chemistry
Malonates - chemistry
Molecular Structure
Organic Chemicals - chemical synthesis
Organic Chemicals - chemistry
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Stereoisomerism
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Zusammenfassung:An enantioselective entry to the skeleton of the tremulane sesquiterpenes is described. The approach features a series of efficient transition metal-catalyzed reactions commencing with an enantioselective rhodium(II)-catalyzed intramolecular cyclopropanation followed by a regioselective allylic alkylation and a diastereoselective rhodium(I)-catalyzed [5 + 2] cycloaddition. This strategy was applied to the first enantioselective syntheses of tremulenediol A and tremulenolide A.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol051945u