Rapid Total Syntheses Utilizing “Supersilyl” Chemistry

Rapid Total Syntheses Utilizing “Supersilyl” Chemistry

In short order: The shortest total syntheses of natural product EBC‐23 (see scheme, PMB=para‐methoxybenzyl, TMS=trimethylsilyl) and a polymethoxy‐1‐alkene to date have been accomplished in just ten total steps each from commercially available chemicals. The syntheses took advantage of highly diaster...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2011-03, Vol.50 (11), p.2610-2612
Hauptverfasser: Albert, Brian J, Yamaoka, Yousuke, Yamamoto, Hisashi
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
aldol reaction
Alkenes - chemical synthesis
Alkenes - chemistry
Molecular Structure
natural products
Pyrans - chemical synthesis
Pyrans - chemistry
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
supersilyl
synthetic methods
Time Factors
total synthesis
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Zusammenfassung:In short order: The shortest total syntheses of natural product EBC‐23 (see scheme, PMB=para‐methoxybenzyl, TMS=trimethylsilyl) and a polymethoxy‐1‐alkene to date have been accomplished in just ten total steps each from commercially available chemicals. The syntheses took advantage of highly diastereoselective supersilyl‐directed cascade polyaldol reactions.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201007210