Iron(III) Catalyzed Direct Synthesis of cis-2,7-Disubstituted Oxepanes. The Shortest Total Synthesis of (+)-Isolaurepan

Prins cyclization of bis-homoallylic alcohols with aldehydes catalyzed by iron(III) salts shows excellent cis selectivity and yields to form 2,7-disubstituted oxepanes. The iron(III) is able to catalyze this process with unactivated olefins. This cyclization was used as the key step in the shortest...

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Bibliographic Details
Published in:Organic letters 2012-12, Vol.14 (23), p.5904-5907
Main Authors: Purino, Martín A, Ramírez, Miguel A, Daranas, Antonio H, Martín, Víctor S, Padrón, Juan I
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Aldehydes - chemistry
Alkenes - chemistry
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Iron Compounds - chemistry
Laurencia - chemistry
Molecular Structure
Oxepins - chemical synthesis
Oxepins - chemistry
Stereoisomerism
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Summary:Prins cyclization of bis-homoallylic alcohols with aldehydes catalyzed by iron(III) salts shows excellent cis selectivity and yields to form 2,7-disubstituted oxepanes. The iron(III) is able to catalyze this process with unactivated olefins. This cyclization was used as the key step in the shortest total synthesis of (+)-isolaurepan.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3028016