Tetrahedron p. 5213 - 5218 (1985)
Update date:2022-08-03
Topics:
Coxon, James M.
Hydes, Graeme J.
Steel, Peter J.
The acid-catalysed ring opening of a number of substituted nopinones to give 4-(2-propyl)cyclohex-2-enones is described.In an application of this reaction use has been made of pinane chirality in the synthesis of R-o-mentha-2,4-diene (13) by fluorosulfonic acid-catalysed rupture of cis-verbanone (8) to (4S,5R)- and (4R,5R)-5-methyl-4(2-propyl)cyclohex-2-enone (9 and 10) followed by reduction-elimination.
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