Tetrahedron

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

B Bollbuck, P Kraft, W Tochtermann

Index: Bollbuck, Birgit; Kraft, Philip; Tochtermann, Werner Tetrahedron, 1996 , vol. 52, # 13 p. 4581 - 4592

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Citation Number: 22

Abstract

Both enantiomers of muscolide (3a b),(R)-(−)-phoracantholide I [(R)-3c] and the homologous (9R)-(−)-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.