10306-22-6Relevant articles and documents
Convenient synthesis of deuterium labelled sesquiterpenes
Duhamel, Nina,Martin, Damian,Larcher, Roberto,Fedrizzi, Bruno,Barker, David
, p. 4496 - 4499 (2016)
Sesquiterpenes are an important class of molecules, with roles ranging from pollination and signalling to defense mechanisms. Despite their apparent importance, the limited number of commercial standards has hindered their study and precise quantification. Herein, we report the syntheses of fourteen labelled sesquiterpenes with a high level of deuterium incorporation (>95%) for applications in MS-based studies.
Oxidative bromination of tricyclic sesquiterpenoids (1S,3S,5R,6S,9S)-5-hydroxy-6,10,10-trimethyl-tricyclo[7.2.0.0 1,6]udecan-2-one and clovane-2β,9α-diol with the HBr-DMSO system
Yusubov,Drygunova,Tkachev
, p. 1419 - 1422 (2001)
Oxidation of tricyclic sesquiterpenoids of the caryophyllene type with the HBr-DMSO system afforded α,β-unsaturated a-bromoketones. Since tricyclic derivatives, unlike simple alicyclic ketones, cannot undergo aromatization, all intermediate oxidation prod
Novel rearrangements of sesquiterpenoid panasinsane derivatives under acidic conditions
Amigo,Collado,Hanson,Hernandez-Galan,Hitchcock,Macias-Sanchez,Mobbs
, p. 4327 - 4332 (2001)
The sesquiterpenoid panasinsane derivatives 11 and 14-16 have been prepared from caryophyllene oxide (7). The novel rearrangement reactions of compounds 11 and 14 under TCNE-catalyzed solvolysis conditions and the reactions of compounds 15 and 16 under superacid conditions (HSO3F/Et2O, -63 °C) have been investigated. The ginsenol derivative 17 is obtained from compounds 11 and 14 under TCNE-catalyzed conditions. The rearrangement of compounds 15 and 16 under superacid conditions leads to the novel sesquiterpene derivatives (1S,4S,7S,10S,11S)-3,3,10,11-tetramethyltricyclo [5.3.1.04,10]undecan-1,11-yl sulfate (19) and (1S,4S,5S,8S)-2,2,4,8-tetramethyl tricyclo[3.3.2.14,8]undecan-11-one (20). The influence of the secondary hydroxyl group at C-5 of the panasinsane derivatives on the course of these rearrangements is discussed.
Biotransformation of caryophyllene oxide by Botrytis cinerea
Duran, Rosa,Corrales, Elena,Hernandez-Galan, Rosario,Collado, Isidro G.
, p. 41 - 44 (1999)
Biotransformation of caryophyllene oxide (1) with B. cinerea afforded 15 products (2-16). Ten of these (3-5, 7, 9-11, and 14-16) are reported here for the first time. The main reaction paths involved stereoselective epoxidation at C-8/C-13 and hydroxylation at C-7. A rearranged compound was found, which was a cyclization product 16 possessing the caryolane skeleton.
