Stereocontrolled [3 + 2] Annulations with Arene Chromium Tricarbonyl Complexes:  Construction of Spirocyclic Compounds Related to Fredericamycin A

Stereocontrolled [3 + 2] Annulations with Arene Chromium Tricarbonyl Complexes:  Construction of Spirocyclic Compounds Related to Fredericamycin A

An efficient method has been developed for the stereocontrolled construction of polycyclic and spirocyclic compounds, including the spirocyclic core of the antitumor agent fredericamycin A. The strategy involves a one-pot aldol addition/Brook rearrangement/cyclization sequence beginning from arene c...

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Veröffentlicht in:Organic letters 2002-06, Vol.4 (12), p.1981-1984
Hauptverfasser: Moser, William H, Zhang, Jian, Lecher, Carl S, Frazier, Tracy L, Pink, Maren
Format: Artikel
Sprache:eng
Schlagworte:
Antibiotics, Antineoplastic - chemistry
Chromium Compounds - chemistry
Isoquinolines - chemistry
Ketones - chemistry
Spiro Compounds - chemistry
Stereoisomerism
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Zusammenfassung:An efficient method has been developed for the stereocontrolled construction of polycyclic and spirocyclic compounds, including the spirocyclic core of the antitumor agent fredericamycin A. The strategy involves a one-pot aldol addition/Brook rearrangement/cyclization sequence beginning from arene chromium tricarbonyl complexes and can formally be described as a [3 + 2] annulation.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol025729m