Shortest Enantioselective Total Syntheses of (+)-Isolaurepinnacin and (+)-Neoisoprelaurefucin

The shortest enantioselective total syntheses of (+)-isolaurepinnacin and (+)-neoisoprelaurefucin have been accomplished. These syntheses were based on a common parallel synthetic strategy using Prins–Peterson cyclization in their core construction. In only one step, a seven-membered ring oxacycle w...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 29; pp. 5271 - 5275
Main Authors Sinka, Victoria, Cruz, Daniel A., Martín, Víctor S., Padrón, Juan I.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 29.07.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Letter
Physical Sciences
Science & Technology
CARBONYL-COMPOUNDS
PRINS CYCLIZATION
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Summary:The shortest enantioselective total syntheses of (+)-isolaurepinnacin and (+)-neoisoprelaurefucin have been accomplished. These syntheses were based on a common parallel synthetic strategy using Prins–Peterson cyclization in their core construction. In only one step, a seven-membered ring oxacycle with the correct cis-stereochemistry ring closure and the Δ4 position of the endocyclic double bond in (+)-isolaurepinnacin was obtained. This unsaturation was also necessary to accede to the bromodioxabicycle on (+)-neoisoprelaurefucin.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01769