Helvetica Chimica Acta p. 1248 - 1253 (1984)
Update date:2022-08-02
Topics:
Guella, Graziano
Cavazza, Marino
Guerriero, Antonio
Pietra, Francesco
Authentic α-santolinenone ( = (+)-(4R)-1(7)-p-menthen-2-one; (+)-1) is made available for the first time in 30 percent overall yield from (+)-(4R)-p-menthene ((+)-2) via the diastereomeric allylic alcohols (+)-4a/(+)-4b, which are oxidized to (+)-1 with Ag2CO3/Celite.Yields are good, except for the last stage; indeed, only alcohol (+)-4a, with equatorial OH-group, undergoes oxidation, and (+)-1 is partly substracted via a hetero Diels-Alder dimerization giving a mixture of the diastereomeric dihydropyrans (+)-5a/(+)-5b.When Cr(VI) reagents are used, (+)-4a/(+)-4b mainly give phelandral (6) and carvotanacetone (7).MnO2 reacts too sluggishly with (+)-4a/(+)-4b.A camphor pyrolyzate, previously thought to be 1 must be a different compound, probably 7.
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Doi:10.1039/c9gc03384j
(2020)Doi:10.1016/S0040-4020(01)82425-X
(1984)Doi:10.1039/b617260a
(2007)Doi:10.1080/00397910600638994
(2006)Doi:10.1021/ol0630651
(2007)Doi:10.1016/j.poly.2006.09.042
(2007)