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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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 124; no. 5; pp. 773 - 775
Main Authors Layton, Mark E, Morales, Carl A, Shair, Matthew D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.02.2002
Amer Chemical Soc
Subjects
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Biological Factors - chemical synthesis
Bridged-Ring Compounds - chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Exact sciences and technology
Molecular Mimicry
Organic chemistry
Physical Sciences
Polycyclic Compounds - chemical synthesis
Preparations and properties
Science & Technology
Stereoisomerism
LONGITHORAX
ENYNE METATHESIS
DIELS-ALDER REACTION
Enantioselectivity
Biomimetic reaction
Transannular reaction
Diels Alder addition
Polycyclic compound
Total synthesis
Macrocycle
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Summary: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.
Bibliography:ark:/67375/TPS-HR0GWVXD-1
istex:C316B99D83555F34C719652394C549FEDA619D89
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja016585u