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.

Intramolecular anodic olefin coupling reactions: the use of bis enol ether substrates

[Moeller, Kevin D.; Tinao, Luzviminda V. Journal of the American Chemical Society, 1992 , vol. 114, # 3 p. 1033 - 1041]

Tris (pentafluorophenyl) boron as an Efficient, Air Stable, and Water Tolerant Lewis Acid Catalyst.

[Ishihara, Kazuaki; Hanaki, Naoyuki; Funahashi, Miyuki; Miyata, Mayumi; Yamamoto, Hisashi Bulletin of the Chemical Society of Japan, 1995 , vol. 68, # 6 p. 1721 - 1730]

1, 5-Dicarbonyl compounds: A general preparation method

[Duhamel, P.; Hennequin, L.; Poirier, J. M.; Tavel, G.; Vottero, C. Tetrahedron, 1986 , vol. 42, # 17 p. 4777 - 4786]