Biomimetic Synthesis of (−)-Longithorone A

Biomimetic Synthesis of (−)-Longithorone A

An enantioseletive, biomimetic synthesis of (−)-longithorone A has been achieved using an intermolecular/transannular Diels-Alder sequence which provides some support for the proposed biosynthesis. The cycloaddition precursors were two [12]-paracyclophanes that were constructed with atropisomer cont...

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Veröffentlicht in:Journal of the American Chemical Society 2002-02, Vol.124 (5), p.773-775
Hauptverfasser: Layton, Mark E, Morales, Carl A, Shair, Matthew D
Format: Artikel
Sprache:eng
Schlagworte:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Biological Factors - chemical synthesis
Bridged-Ring Compounds - chemical synthesis
Chemistry
Exact sciences and technology
Molecular Mimicry
Organic chemistry
Polycyclic Compounds - chemical synthesis
Preparations and properties
Stereoisomerism
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Beschreibung
Zusammenfassung:An enantioseletive, biomimetic synthesis of (−)-longithorone A has been achieved using an intermolecular/transannular Diels-Alder sequence which provides some support for the proposed biosynthesis. The cycloaddition precursors were two [12]-paracyclophanes that were constructed with atropisomer control during ene−yne metathesis macrocyclizations.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja016585u