Synthesis of the C4-Epi-Lomaiviticin B Core Reveals Subtle Stereoelectronic Effects

Synthesis of the C4-Epi-Lomaiviticin B Core Reveals Subtle Stereoelectronic Effects

An efficient synthesis of the C4-epi-lomaiviticin B core is reported. The synthesis features a diastereoselective anionic formal furan Diels–Alder reaction and a stereoselective oxidative enolate dimerization. During the investigation, subtle yet critical stereoelectronic effects imparted by the C4-...

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Veröffentlicht in:Organic letters 2013-05, Vol.15 (10), p.2390-2393
Hauptverfasser: Lee, Amy S, Shair, Matthew D
Format: Artikel
Sprache:eng
Schlagworte:
Cycloaddition Reaction
Fluorenes - chemical synthesis
Fluorenes - chemistry
Molecular Structure
Oxidation-Reduction
Stereoisomerism
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Zusammenfassung:An efficient synthesis of the C4-epi-lomaiviticin B core is reported. The synthesis features a diastereoselective anionic formal furan Diels–Alder reaction and a stereoselective oxidative enolate dimerization. During the investigation, subtle yet critical stereoelectronic effects imparted by the C4-stereocenter were observed.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol400832r