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Nature-like odorants by stereoselective ring enlargement of cyclohexanone and cyclododecanone

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
52
Issue
13
Identifiers
DOI: 10.1016/0040-4020(96)00170-6
Keywords
  • Article

Abstract

Abstract Both enantiomers of muscolide ( 3a b ), ( R)-(−)-phoracantholide I [ (R)- 3c ] and the homologous (9 R)-(−)-9-tetradecanolide [ (R)- 3d ] were synthesized by ring enlargement of cyclohexanone ( 6c) and cyclododecanone ( 6a). The ring-enlargement sequence was improved by oxidation of 9 10 with ruthenium tetroxide and reduction of 8 using catecholborane.

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