76735-22-3Relevant academic research and scientific papers
Chiral 2α,4-dihydroxy-1,8-cineole as a possum urinary metabolite
Carman, Raymond M.,Rayner, Anthony C.
, p. 1 - 6 (2007/10/03)
Both enantiomers of 2α,4-dihydroxy-1,8-cineole (2) have been synthesized. The enantiomer present in possum urine is the (-)-(1R,2R,4R)-isomer (2′). This diol is biosynthesized in the possum from (1R,2R,4S)-2α-hydroxy-1,8-cineole (18).
PREPARATION OF BIOLOGICALLY ACTIVE SUBSTANCES AND ANIMAL AND MICROBIAL METABOLITES FROM MENTHOLS, CINEOLES AND KAURANES
Asakawa, Yoshinori,Matsuda, Reiko,Tori, Motoo,Hashimoto, Toshihiro
, p. 3861 - 3870 (2007/10/02)
Six monoterpenoids, l-menthol, l-menthyl acetate, iso-menthol, neo-menthol, 1,4-cineole and 1,8-cineole and one diterpene hydrocarbon, ent-kaurene were oxidized by meta-chloroperbenzoic acid or dry ozone to give various hydroxylated products and their structures elucidated by NMR spectroscopy.Some hydroxylated menthols showed plant growth inhibitory and strong mosquito repellent activity.Among the hydroxylated cineoles, microbial and animal metabolites of cineoles were included.From ent-kauranes, a plant growth inhibitory diterpene alcohol, (-)-16α-hydroxy kaurane was obtained along with 16α-kauran-13α-ol.
Carbonyl Transposition and Regio- and Stereo-specific Syntheses of New Alcohols, Amino-alcohols, and Ketones in the Monoterpenoid 1,3,3-Trimethyl-2-oxabicyclooctane
Bondavalli, Francesco,Schenone, Pietro,Ranise, Angelo,Lanteri, Silvia
, p. 2626 - 2630 (2007/10/02)
An efficient transposition of carbonyl group R1-CO-CH2-R2 -> R1-CH2-CO-R2 in the 1,3,3-trimethyl-2-oxabicyclooctane system was carried out via hydroboration-oxidation of 6-dialkylamino-1,3,3-trimethyl-2-oxabicyclooct-5-enes (3a-c), which gave regio- and stereo-specifically 6-cis-dialkylamino-1,3,3-trimethyl-2-oxabicyclooctan-5-trans-ols (4a-c) in high yield.Cope reaction on the N-oxide (5b) obtained from the amino-alcohol (4b) with hydrogen peroxide led to 1,3,3-trimethyl-2-oxabicyclooctan-5-one (6), the other possible isomer of the long-known 1,3,3-trimethyl-2-oxabicyclooctan-6-one (1b).The ketone (6) was also obtained from 1,3,3-trimethyl-2-oxabicyclooct-5-ene (2) via its trans-epoxide (11), lithium aluminium hydride reduction at 160-165 deg C of which gave stereo- and regio-specifically 1,3,3-trimethyl-2-oxabicyclooctan-5-trans-ol (9b).Chromic acid oxidation of (9b) and (4a-c) under various conditions gave the ketone (6) and the amino-ketones (7a-c), respectively.Lithium aluminium hydride reduction of (6) and (7a-c) afforded stereospecifically the cis-alcohol (9a) and 6-cis-dialkylamino-1,3,3-trimethyl-2-oxabicyclooctan-5-cis-ols (8a-c), respetively.Hydroboration-oxidation of the alkene (2) was not regiospecific, giving a 3:1 mixture of the trans-alcohols (9b) and (10b), respectively.
