68832-35-9

Upstream product

• 61824-50-8 (Z)-(1R,9S)-4,11,11-Trimethyl-8-methylene-bicyclo[7.2.0]undec-3-en-5-one 
• 372-97-4 farnesyl pyrophosphate 

Downstream Products

• 1217184-42-3 (1S,2S,5R,8R)-4,4,8-trimethyltricyclo[6.3.1.0(2,5)]dodecanyl acetate 
• 57082-24-3 caryophyllene acetate 
• 58404-89-0 β-caryolanol 
• 469-92-1 (-)-Clovene 
• 88514-14-1 (1R,6R,10S)-5,12,12-Trimethyl-9-methylene-4-oxa-tricyclo[8.2.0.0^3,5]dodecan-6-ol 
• 19431-76-6 caryophyllenol-II 
• 1139-30-6 caryophyllene epoxide 
• 32214-91-8 Acetic acid (Z)-(1R,5R,9S)-4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-3-en-5-yl ester 
• 19431-76-6 caryophyllenol-I 
• 19431-79-9 (1S,5S,9R)-10,10-Dimethyl-2,6-dimethylene-bicyclo[7.2.0]undecan-5-ol 

Relevant academic research and scientific papers

An Unusual Skeletal Rearrangement in the Biosynthesis of the Sesquiterpene Trichobrasilenol from Trichoderma

The skeletons of some classes of terpenoids are unusual in that they contain a larger number of Me groups (or their biosynthetic equivalents such as olefinic methylene groups, hydroxymethyl groups, aldehydes, or carboxylic acids and their derivatives) than provided by their oligoprenyl diphosphate precursor. This is sometimes the result of an oxidative ring-opening reaction at a terpene-cyclase-derived molecule containing the regular number of Me group equivalents, as observed for picrotoxan sesquiterpenes. In this study a sesquiterpene cyclase from Trichoderma spp. is described that can convert farnesyl diphosphate (FPP) directly via a remarkable skeletal rearrangement into trichobrasilenol, a new brasilane sesquiterpene with one additional Me group equivalent compared to FPP. A mechanistic hypothesis for the formation of the brasilane skeleton is supported by extensive isotopic labelling studies.

EIGHT NEW XENIA DITERPENOIDS FROM THREE SOFT CORALS OF THE RED SEA

Investigation of the terpenoid content of three soft corals from the Gulf of Eilat (THe Red Sea), Xenia macrospiculata, X. obscuronata and X. lilielae resulted in the isolation of 8 new diterpens.Two of the new compounds belong to the xeniolides (xenialactol-D (10a) and xeniolide-E (13)) and the other six (4,14-diepoxyxeniaphyllene (15), 4,5-epoxyxeniaphyllan-14,15-diol (17), 4,14-diepoxy-xeniaphyllenol-A (21a), xeniaphyllenol-B (23a), xeniaphyllenol-C (24a) and xeniaphyllantriol (25) are new xeniaphyllanes (prenylated caryophyllanes).The structure determination of the various compounds is based on chemical transformations as well as on the 1H and 13C NMR spectra.Several known caryophyllene derivatives have been synthesised for 13C NMR spectra and chemical comparisons.The 13C NMR has proven to be an excellent probe for structural and stereochemical determinations.