Total Synthesis of (±)-Bipinnatin J

Total Synthesis of (±)-Bipinnatin J

The total synthesis of (±)-bipinnatin J was achieved through a concise route that features the use of a silver ion promoted SN1-type γ-alkylation of a siloxyfuran and a diastereoselective Cr(II)-mediated macrocyclization to provide bipinnatin J (1), wherein the remote furanone stereocenter at C10 in...

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Veröffentlicht in:Organic letters 2006-02, Vol.8 (3), p.543-545
Hauptverfasser: Huang, Qinhua, Rawal, Viresh H
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Cyclization
Diterpenes - chemical synthesis
Diterpenes - chemistry
Furans - chemistry
Molecular Structure
Stereoisomerism
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Zusammenfassung:The total synthesis of (±)-bipinnatin J was achieved through a concise route that features the use of a silver ion promoted SN1-type γ-alkylation of a siloxyfuran and a diastereoselective Cr(II)-mediated macrocyclization to provide bipinnatin J (1), wherein the remote furanone stereocenter at C10 induced the relative stereochemistry of the two additional stereocenters.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol053054s