Determination of the Absolute Configuration of (+)-2,7(14),10-Bisabolatrien- 1-ol-4-one from Japanese Cedar,Cryptomeria japonica

Repellents in the Japanese Cedar,Cryptomeria japonica, against the Pill-bug,Armadillidium vulgare

“…Judging from these results, the speciˆc rotation value ([a]D 20 +1309 , c＝1.0, MeOH), and H-H, CH COSY, and COLOC spectra, this compound was identiˆed as (+)-2,7(14),10-bisabolatrien-1-ol-4-one. The spectral data were identical with those in the literature, 7,9,10) for (1S,6R)-2,7(14),10-bisabolatrien-1-ol-4-one (Fig. 4).…”

“…10) Its only known biological activity is the antifeeding activity 7) against Acusta despesta, a snail species that is a pest for many vegetables and several other types of crops throughout the world.…”

Selective synthesis of carvone and cryptomerlone from α-pinene

“…Removal of the silyl protection and subsequent treatment with PDC completed the synthesis of cryptomerlone 9, the spectral properties of which agreed with those in the literature [3]. Thus, we carried out a specific synthesis of carvone and cryptomerlone using electrochemical oxidation of α-pinene to construct the p-menthane fragment of the target products.…”

“…The more polar compound eluted from the column was sobrerol diacetate (3). Ester 3 eliminates AcOH on boiling in Ac 2 O to form an additional amount of 2.…”

Concise Synthesis of an Antifeedant Sesquiterpene againstLocusta migratoria

“…1) Based on the bioassay results, they reported that 2 was essential for the antifeeding activity against L. migratoria, while 1 played a role in supporting the activity of 2. 1) Compound 1 had originally been reported as a chemical constituent of C. japonica by Nagahama et al, 2) and its absolute stereochemistry was later determined by Kim et al 3) Compound 2 was also previously isolated from C. japonica by Nagahama et al, 4) and its absolute stereochemistry was unambiguously determined through its first enantioselective synthesis performed by Nakahata et al in 2008. 5) More recently, other enantioselective syntheses of 1 and 2 have been disclosed by Shimizu and Kuwahara.…”