Total Synthesis of (+)-Clavilactone A and (−)-Clavilactone B by Ring-Opening/Ring-Closing Metathesis

Total Synthesis of (+)-Clavilactone A and (−)-Clavilactone B by Ring-Opening/Ring-Closing Metathesis

The enantioselective total synthesis of natural enantiomers of clavilactones A and B has been achieved. A key feature of the synthesis is the use of a ring-opening/ring-closing metathesis, which allows the one-pot transformation of a strained cyclobutenecarboxylate into a γ-butenolide.

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Veröffentlicht in:Organic letters 2013-11, Vol.15 (21), p.5582-5585
Hauptverfasser: Takao, Ken-ichi, Nanamiya, Ryuki, Fukushima, Yuuki, Namba, Ayumi, Yoshida, Keisuke, Tadano, Kin-ichi
Format: Artikel
Sprache:eng
Schlagworte:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemistry
Catalysis
Cyclobutanes - chemistry
Lactones - chemical synthesis
Lactones - chemistry
Molecular Structure
Stereoisomerism
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Zusammenfassung:The enantioselective total synthesis of natural enantiomers of clavilactones A and B has been achieved. A key feature of the synthesis is the use of a ring-opening/ring-closing metathesis, which allows the one-pot transformation of a strained cyclobutenecarboxylate into a γ-butenolide.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4027842