Enantioselective access to benzannulated spiroketals using a chiral sulfoxide auxiliary

This article describes our efforts to develop an asymmetric synthesis of bisbenzannulated spiroketals using a chiral sulfoxide auxiliary. Our primary focus was on the synthesis of the 3H-spiro[benzofuran-2,2'-chroman] ring system, the spirocyclic core of the rubromycin family. Our strategy empl...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2013-08, Vol.11 (31), p.5147-5155
Main Authors: Aitken, Harry R M, Furkert, Daniel P, Hubert, Jonathan G, Wood, James M, Brimble, Margaret A
Format: Article
Language:English
Subjects:
Benzene - chemistry
Furans - chemistry
Molecular Structure
Quinones - chemistry
Safrole - analogs & derivatives
Safrole - chemistry
Spiro Compounds - chemistry
Stereoisomerism
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Summary:This article describes our efforts to develop an asymmetric synthesis of bisbenzannulated spiroketals using a chiral sulfoxide auxiliary. Our primary focus was on the synthesis of the 3H-spiro[benzofuran-2,2'-chroman] ring system, the spirocyclic core of the rubromycin family. Our strategy employed the use of lithium-halogen exchange on a racemic bromospiroketal in order to attach a chiral sulfoxide, thus producing two diastereomers. The diastereomers were separable, enabling isolation of each spiroketal enantiomer. Subsequent cleavage of the sulfoxide group from each diastereomer yielded the respective parent spiroketal in high enantiopurity.
ISSN:1477-0520
1477-0539
DOI:10.1039/c3ob41065j