6994-88-3

Upstream product

• 128291-28-1 2'-isopropenylpotassium 
• 590-86-3 isovaleraldehyde 
• 128291-26-9 B-isoprenyldiisopinocampheylborane 
• 62961-64-2 D-(-)-diisopropyl tartrate 
• 122038-72-6 dimethoxyisoprenylborane 
• 57566-87-7 (R)-5-Isobutyl-3-phenylselanylmethyl-dihydro-furan-2-one 
• 129084-78-2 (2'S)-2-<2'<(tert-butyl)dimethylsilyloxy>-4'-methylpentyl>buta-1,3-diene 
• 143998-50-9 2,2-Dimethyl-propionic acid (1S,4S)-4-hydroxy-1,6-dimethyl-2-methylene-heptyl ester 
• 128291-26-9 B-isoprenyldiisopinocampheylborane 
• 57566-87-7 (S)-5-Isobutyl-3-phenylselanylmethyl-dihydro-furan-2-one 
• 71092-51-8 (2-methylene-3-butenyl)-trimethyltin 
• 57566-86-6 4-hydroxy-6-methyl-2-(phenylselanyl-methyl)-heptanal 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 23691-13-6 2-(bromomethyl)buta-1,3-diene 

Relevant academic research and scientific papers

Enantioselective iridium-catalyzed carbonyl isoprenylation: Via alcohol-mediated hydrogen transfer

Highly enantioselective iridium catalyzed carbonyl (2-vinyl)allylation or "isoprenylation" is achieved via hydrogen auto-transfer or 2-propanol-mediated reductive coupling from primary alcohol or aldehyde reactants, respectively. Using this method, asymmetric total syntheses of the terpenoid natural products (+)-ipsenol and (+)-ipsdienol were achieved.

Enantioselective Isoprenylboration Reaction of Aldehydes Catalyzed by a Chiral Phosphoric Acid

The BINOL-derived chiral phosphoric acid (R)-TRIP is utilized as an organocatalyst in the asymmetric isoprenylboration reaction of aldehydes, wherein hydrogen-bond interactions play a key role in the control of enantioselectivity. A wide arrays of enantioenriched dienyl homoallyl alcohols, including two natural products (?)-Ipsdienol and (?)-Ipsenol, have been successfully constituted. The synthetic application to chiral isoprenylated isobenzofuranone, vinyloxirane and cyclohexene derivatives has also been disclosed. (Figure presented.).

METHOD FOR PRODUCING MONOTERPENE AND MONOTERPINOID COMPOUNDS AND USE THEREOF

In various embodiments, the present disclosure provides a method and enzyme for forming various compounds, such as monoterpenes and monoterpenoid compounds. In a specific example, the present disclosure provides a method for producing one or more of (?)-ipsdienol, (?)-ipsenol, ipsenone, and ipsdienone. The present disclosure also provides methods of using compounds formed from the disclosed method and enzyme.

Dienyl homoallyl alcohols via palladium catalyzed ene-type reaction of aldehydes with 1,3-dienes

The combination of Pd catalyst and Xantphos ligand in the presence of Et3B nicely promotes the allylation of aldehydes with conjugated dienes to provide dienyl homoallyl alcohols in excellent yields. The reaction occurs selectively at the C-C double bond bearing higher electron density.

Pd-catalyzed cross-coupling of allylsilane-vinylcopper species with aryl and vinyl halides: the first total synthesis of (-)-nomadone

The reaction of allene with a lower order silylcuprate 3 leads to an allylsilane-vinylcopper intermediate 4, which undergoes palladium-catalyzed cross-coupling reaction with both vinyl and aryl halides. The influence of several factors such as the nature

Transformation of carboxylic acid esters into 2-substituted allyl halides through tertiary cyclopropyl sulfonates. Application in the synthesis of (±)-ipsenol and (±)-ipsdienol, components of Ips typographus spark beetle pheromone

Cyclopropanation of the ester group in ethyl 3-chloropropanoate and subsequent cleavage of the three-membered carbocycle in intermediate 1-(2-chloroethyl)cyclopropyl methanesulfonate gave 2-bromomethyl-4-chlorobut-1- ene, and the latter was used as key intermediate in the synthesis of racemic ipsenol and ipsdienol which are components of Ips typographus L. European spruce spark beetle pheromone. Pleiades Publishing, Inc., 2006.

Intramolecular coupling of vinyl ether and olefins or acetylenes with Ti(II) reagent. Regio- and stereo-selective vinyltitanation of carbon-carbon multiple bonds

Treatment of m-alkenyl (or m-alkynyl) vinyl ethers (m = 3,4) with a Ti(II) reagent generated most likely bicyclic oxatitana-cycles, which eliminate the alkoxide tether to effect the selective vinyltitanation of the alkene or alkyne moiety to give m-vinyl-

Proline-catalyzed asymmetric aldol reactions between ketones and alpha-unsubstituted aldehydes.

[reaction: see text] With this communication we extend the methodology of proline-catalyzed direct asymmetric aldol reactions to include alpha-unsubstituted aldehydes as acceptors. This important aldehyde class gives the corresponding aldols in 22-77% yield and up to 95% ee when the reactions are performed in pure acetone or in ketone/chloroform mixtures. On the basis of these results we have developed a concise new synthesis of (S)-ipsenol.

Allylsilane-vinylcopper reagents: Palladium-mediated coupling with alkenyl halides. Synthesis and photochemical [2+2] cyclization of (±)-Ipsdienol

Reaction of phenyldimethylsilyl-copper with 1,2-propadiene followed by Pd0 catalyzed coupling of the resulting copper intermediate with alkenyl halides affords allylsilane-containing dienes in high yield. Coupling with vinyl bromide gives 2-phenyldimethylsilylmethylbuta-1,3-diene which is an isoprenyl building block for the synthesis of (±)-Ipsenol and (±)-Ipsdienol, the aggregation pheromones of the Ips bark beetle. The photochemical [2+2] cyclization of Ipsdienol was also studied.

Catalytic asymmetric allylic transfer reactions for the Enantioselective synthesis of dienyl and enynyl alcohols

Efficient catalytic asymmetric allylic transfer reactions of achiral aldehydes with 2-ethynyl- and 2-ethenyl-2-propenyl-stannane promoted by BINOL-TiIV complex with synergetic reagent are achieved for the synthesis of homoenynyl- and dienyl alcohols with high levels of enantioselectivity. The range of enantioselectivity is 84-99% ee with good chemical yields. The application of catalytic asymmetric dienylation in a single operation was exemplified by the enantioselective synthesis of naturally occurring (-)-Ipsdienol and (-)-Ipsenol.