Regioselective Synthesis of the Tricyclic Core of Lateriflorone

Regioselective Synthesis of the Tricyclic Core of Lateriflorone

An efficient synthetic approach to the tricyclic core 8 of lateriflorone is described. Essential to the synthesis was the implementation of a biomimetic tandem Claisen/Diels−Alder reaction that produced the desired tricyclic scaffold as a single isomer. A rationalization of the excellent regio and s...

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Veröffentlicht in:Organic letters 2003-05, Vol.5 (9), p.1491-1494
Hauptverfasser: Tisdale, Eric J, Li, Hongmei, Vong, Binh G, Kim, Sun Hee, Theodorakis, Emmanuel A
Format: Artikel
Sprache:eng
Schlagworte:
Cyclization
Garcinia - chemistry
Molecular Conformation
Polycyclic Compounds - chemical synthesis
Spiro Compounds - chemical synthesis
Spironolactone - chemical synthesis
Stereoisomerism
Xanthenes - chemistry
Xanthones
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Zusammenfassung:An efficient synthetic approach to the tricyclic core 8 of lateriflorone is described. Essential to the synthesis was the implementation of a biomimetic tandem Claisen/Diels−Alder reaction that produced the desired tricyclic scaffold as a single isomer. A rationalization of the excellent regio and stereoselectivity of this transformation is also proposed.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol034276y