NATURE-LIKE ODORANTS BY STEREOSELECTIVE RING ENLARGEMENT OF CYCLOHEXANONE AND CYCLODODECANONE

Authors
BOLLBUCK B KRAFT P TOCHTERMANN W
Citation
B. Bollbuck et al., NATURE-LIKE ODORANTS BY STEREOSELECTIVE RING ENLARGEMENT OF CYCLOHEXANONE AND CYCLODODECANONE, Tetrahedron, 52(13), 1996, pp. 4581-4592
Citations number
49
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
13
Year of publication
1996
Pages
4581 - 4592
Database
ISI
SICI code
0040-4020(1996)52:13<4581:NOBSRE>2.0.ZU;2-S
Abstract
Both enantiomers of muscolide (3a/b), (R)-(-)-phoracantholide I [(R)-3 c] and the homologous (9R)-(-)-9-tetradecanolide [(R)-3d] were synthes ized 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.