Toward the Synthesis of the Carbacylic ansa Antibiotic Kendomycin

The convergent synthesis of a benzofuran analog of the carbacyclic ansa compound kendomycin has been achieved by assembling three major fragments by means of epoxide opening and directed ortho lithiation. The crucial tetrahydropyran ring was formed by a highly stereoselective cationic cyclization. A...

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Bibliographic Details
Published in:Proceedings of the National Academy of Sciences - PNAS 2004-08, Vol.101 (33), p.11980-11985
Main Authors: Mulzer, Johann, Pichlmair, Stefan, Green, Martin P., Maria M. B. Marques, Martin, Harry J., Nicolaou, Kyriacos C.
Format: Article
Language:English
Subjects:
Alcohols
Aldehydes
Analog
Ansae
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Antibiotics
Benzofurans
Bromides
Chemical compounds
Chemical synthesis
Chemistry
Chemistry, Organic - methods
Chlorides
Epoxy compounds
Models, Molecular
Molecular Structure
Natural Product Synthesis Special Feature
Oxidation
Physical Sciences
Rifabutin - analogs & derivatives
Rifabutin - chemical synthesis
Rifabutin - chemistry
Rotation
Stereoisomerism
Tetrahedrons
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Summary:The convergent synthesis of a benzofuran analog of the carbacyclic ansa compound kendomycin has been achieved by assembling three major fragments by means of epoxide opening and directed ortho lithiation. The crucial tetrahydropyran ring was formed by a highly stereoselective cationic cyclization. Analysis of all synthesized tetrahydropyran-arene compounds reveals a hindered sp2- sp3rotation, which results in rotational isomers or atropisomers affecting macrocyclization reactions. The latter could only be achieved by means of Horner-Wadsworth-Emmons olefination.
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.0401503101