7733-91-7

Upstream product

• 3796-70-1 trans geranyl acetone 
• 22842-10-0 2-methylhept-2-en-6-yne 
• 97071-77-7 (Z)-6-iodo-10-methyl-5,9-undecadien-2-one 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 15146-94-8 5-chloro-2-pentanol 
• 121424-59-7 6,10-dimethyl-9-undecene-2,6-diol 

Downstream Products

• 3796-70-1 trans geranyl acetone 
• 81795-13-3 (2S, 3R, 6R; 2R, 3S, 6S) 2.6-dimethyl-2-(4-methylpent-3-enyl)-3-phenylselenooxane 
• 81795-14-4 (2S, 5R; 2R, 5S) 2-(1.5-dimethyl-1-selenophenyl-hex-5-enyl)-5-methyl-oxolane 
• 81795-14-4 (2S,5S)-2-(1,5-Dimethyl-1-phenylselanyl-hex-4-enyl)-5-methyl-tetrahydro-furan 
• 13720-37-1 dihydro-α-ionol 
• 446293-91-0 4-(2,6,6-trimethyl-cyclohex-1-enyl)-butan-2-ol 
• 3239-35-8 (E)-6,10-dimethylundeca-5,9-dien-2-yl acetate 
• 947587-70-4 C₂₃H₃₆O₃ 
• 3796-62-1 (5E)-6,10-dimethylundeca-5,9-dien-2-one ethylene acetal 
• 81795-15-5 6β-phenylseleno-2α.5.5.8aβ-tetramethyl-3.4.4aα.5.6.7.8aβ-octahydro-2-H-1-benzopyran 
• 81795-15-5 6β-phenylseleno-2β.5.5-8aβ-tetramethyl-3.4.4.aα.5.6.7.8.8aα-octahydro-2H-1-benzopyran 
• 1138324-52-3 (R)-(E)-6,10-dimethyl-5,9-undecadien-2-yl acetate 
• 53837-34-6 (S)-(+)-geranylacetol 
• 55968-43-9 2,6-dimethyl-10-(p-tolyl)-2,6(E)-undecadiene 

Relevant academic research and scientific papers

Synthesis of a potential enzyme-specific inhibitor of squalene synthase

A multi-step synthesis of phosphinylphosphonate analogue 12 of the proposed farnesyl-farnesyl-enzyme (FFE) intermediate in the enzymatic conversion of farnesyl pyrophosphate to squalene is described.In addition, evidence is presented of the inhibitory effect of 12 on squalene synthase.

BIOSYNTHESIS OF CHEMICALLY DIVERSIFIED NON-NATURAL TERPENE PRODUCTS

The disclosure relates to compounds of the formulae (l)-(IV) and their use as substrates for making terpenoids. New substrates for terpene biosynthesis and methods for making new types of terpenes are described herein. Diterpenes occupy a unique molecular

Asymmetric Cation-Olefin Monocyclization by Engineered Squalene–Hopene Cyclases

Squalene–hopene cyclases (SHCs) have great potential for the industrial synthesis of enantiopure cyclic terpenoids. A limitation of SHC catalysis has been the enzymes’ strict (S)-enantioselectivity at the stereocenter formed after the first cyclization step. To gain enantio-complementary access to valuable monocyclic terpenoids, an SHC-wild-type library including 18 novel homologs was set up. A previously not described SHC (AciSHC) was found to synthesize small amounts of monocyclic (R)-γ-dihydroionone from (E/Z)-geranylacetone. Using enzyme and process optimization, the conversion to the desired product was increased to 79 %. Notably, analyzed AciSHC variants could finely differentiate between the geometric geranylacetone isomers: While the (Z)-isomer yielded the desired monocyclic (R)-γ-dihydroionone (>99 % ee), the (E)-isomer was converted to the (S,S)-bicyclic ether (>95 % ee). Applying the knowledge gained from the observed stereodivergent and enantioselective transformations to an additional SHC-substrate pair, access to the complementary (S)-γ-dihydroionone (>99.9 % ee) could be obtained.

Adult Monochamus alternatus attractant and preparation method thereof

The invention discloses an adult Monochamus alternatus attractant and a preparation method thereof, and belongs to the technical field of insect attractant production. The main effective component ofthe adult Monochamus alternatus attractant is an artificially synthesized compound having a high attracting effect on Monochamus alternatus, and comprises a botanical compound and a diluent. The attractant has the advantages of reasonability in proportioning and high trapping efficiency, and can efficiently monitor, trap and kill adult Monochamus alternatus. The invention also provides a synthesisroute and the synthesis method of the artificially synthesized compound with the high attracting effect on Monochamus alternatus. The adult Monochamus alternatus attractant is prepared from geranylacetone, a reducing agent and acetyl chloride. The method has the advantages of simple raw materials, environmentally friendly steps, high production efficiency and good industrial application prospect,can be used for preparing the adult Monochamus alternatus attractant on a large scale, and has high practical application values.

Biomimetic syntheses from squalene-like precursors: Synthesis of ent- abudinol B and reassessment of the structure of muzitone

We achieved the stereoselective syntheses of two different structural patterns corresponding to the enantiomers of the marine natural products abudinol B and muzitone, by developing two-directional tandem biomimetic cyclizations of polyepoxides of squalene analogues in which one alkene was functionalized as an enolsilane. In the course of this work, we demonstrated that the structure of muzitone was misassigned.

Enantioselective synthesis and absolute configuration of the sex pheromone of Hedypathes betulinus (Coleoptera: Cerambycidae)

The male-produced sex pheromone of Hedypathes betulinus was identified as a mixture of (E)-6,10-dimethyl-5,9-undecadien-2-one (geranylacetone) (1) and its respective alcohol (2) and acetate (3). Kinetic resolution of alcohol (2) promoted by CAL-B in organic media provided both, (R)-(-)-(E)-6,10-dimethyl-5,9- undecadien-2-yl acetate (3) and (S)-(+)-(E)-6,10-dimethyl-5,9-undecadien-2-ol (2) in high enantiomeric purity. Comparative GC analysis using a chiral column revealed the natural constituents as being (R)-(3) and a mixture of (R)- and (S)-(2) in a ratio of 82.3% and 17.6%, respectively.

Male produced pheromone in Tetropium fuscum (F.) and Tetropium cinnamopterum (Kirby) (Coleoptera: Cerambycidae)

Described herein is (E)-6,10-dimethyl-5,9-undecadien-2-ol (geranyl acetol), termed here fuscumol, which has been identified as a male-produced pheromone emitted by Tetropium fuscum (F.) and Tetropium cinnamopterum. Also described are novel derivatives thereof e.g. esters, methods for the synthesis thereof and to a composition comprising fuscumol plus host volatiles e.g. a synthetic blend of monoterpenes plus ethanol, for attracting male and female T. fuscum and female T. cinnamopterum.

Total syntheses of durgamone, nakorone, and abudinol B via biomimetic oxa- and carbacyclizations

The first biomimetic total syntheses of ent-nakorone, ent-durgamone, and ent-abudinol B were accomplished by combining features of tandem polyepoxide cyclization with biomimetic polyene cyclization. The present biomimetic synthesis route offers efficient

First total synthesis of (±) Hedaol B

Hedaol B, a new bisnorditerpene isolated from the Japanese brown alga Sargassum. sp., was first synthesized starting from geranyl acetone, alkylation of silyl cyanide as the key step.

Chlorosulfonic acid as a convenient electrophilic olefin cyclization agent

Among several sulfonic acids studied (MeSO3H, p-TsOH, H2SO4, ClSO3H, FSO3H), the scarcely used chlorosulfonic acid showed to be an efficient agent for electrophilic olefin cyclizations with internal nucleophilic termination, in a similar manner that is well-established with fluorosulfonic acid. Its availability, lower price and relatively lesser handling problems makes ClSO3H an advantageous cyclizing agent particularly for high-scale applications. The stereochemical outcome of these cyclizations has been rationalized.