New Sesquiterpenoids from Cabreuva Oil

Abstract

Six sesquiterpenoids 1 4 , formally derived from (+)-(S)-nerolidol by oxidative cyclization, have been isolated for the first time from commercial cabreuva oil. Whereas the two tetrahydrofurans 5 and 6 have already been described, the four bicyclic ethers (cabreuva oxides A-D) 1 4 are new. The structures of 1 4 are confirmed by synthesis and their absolute configurations are shown to be 3s. The organoleptic properties of the synthetic cabreuva oxides are discussed.

Identification and Characterization of the Linalool/Nerolidol Synthase from Streptomyces clavuligerus

“…Racemic linalool and racemic nerolidol were purchased from Wako (Osaka, Japan). (3S)-(E)-Nerolidol from cabreuva oil [37] was obtained from Mitsuhiko Fujiwara (Takasago International Corporation, Tokyo, Japan).…”

Unusual Reactions of (+)‐Car‐2‐ene and (+)‐Car‐3‐ene with Aldehydes on K10 Clay

“…Without solvent, the reaction of 2 with 4-methoxybenzaldehyde for Scheme 4. Cyclization of Compound 15 [15] 3 days led to insignificantly increased yields of 16a,b and 17 (4% at 60% conversion of 2).…”

“…Compound 14 (Scheme 4), which is structurally related to 13a,b, was previously obtained as a by-product of cyclizations of compound 15, and it is also found in trace amounts in cabreuva oil [15].…”

75 Jahre Riechstoff‐ und Aroma‐Chemie im Spiegel der Helvetica Chimica Acta. Teil I

“…[86] [87] verkniipft werden. Die diastereoisomeren sesquiterpenoiden Monotetrahydrofuran-Derivate des Nerolidols 55 und 56 konnten im Osmanthus-01 entdeckt [88] und spater auch im Cabreuva-01 als Naturstoff nachgewiesen werden [89]. …”

“…Vom Monocyclonerolidol leiten sich das spirocyclische Cabreuva-oxid (61) [89], das verwandte Dactyloxen (62) [92] ebenso wie das pyranoide Caparrapi-oxid (63) ab [93]. Ihr Vorkommen in den entsprechenden atherischen Olen wird im nachsten Kap.…”