109429-39-2

Upstream product

• 109322-33-0 (Z)-5-((2S,3R)-3-Ethyl-oxiranyl)-pent-3-en-2-one 
• 109322-32-9 5-((2S,3R)-3-Ethyl-oxiranyl)-pent-3-yn-2-one 
• 250359-36-5 (2R,4RS,6S,7R)-exo-7-ethyl-5-methyl-4-phenylseleno-6,8-dioxabicyclo[3.2.1]octane 
• 6261-22-9 pent-2-yn-1-ol 
• 106034-58-6 [(2S,3R)-3-ethyloxiran-2-yl]methanol 
• 109322-31-8 5-((2S,3R)-3-Ethyl-oxiranyl)-pent-3-yn-2-ol 
• 109322-30-7 (2S,3R)-2,3-epoxypentyl triflate 
• 109429-38-1 (Z)-5-((2R,3S)-3-Ethyl-oxiranyl)-pent-3-en-2-one 
• 108740-32-5 (2R,3S)-3-ethyl(oxiranemethanol) 
• 109322-31-8 5-((2R,3S)-3-Ethyl-oxiranyl)-pent-3-yn-2-ol 
• 109429-37-0 5-((2R,3S)-3-Ethyl-oxiranyl)-pent-3-yn-2-one 
• 109322-30-7 (2R,3S)-2,3-epoxypentyl triflate 
• 109322-33-0 (Z)-5-((2S,3S)-3-Ethyl-oxiranyl)-pent-3-en-2-one 
• 109987-12-4 (+/-)-(E)-6-nonen-3-yn-2-ol 

Relevant academic research and scientific papers

Asymmetric synthesis of (?)-dehydro-exo-brevicomin with a photoisomerisation-intramolecular acetalisation sequence

We herein report a novel, short asymmetric synthesis of (?)-dehydro-exo-brevicomin (DHB,1), a sex pheromone isolated from house mice, in 44% overall yield, the highest yield reported so far, over eight steps fromtrans-3-hexen-1-ol (7). We successfully prepared the target molecule (?)-1from spontaneous intramolecular acetalisation after the photoisomerisation oftrans-enone6, which generated the correspondingcis-enone5in situ, the possible biosynthetic precursor of DHB.

Protective group-free syntheses of (±)-frontalin, (±)-endo-brevicomin, (±)-exo-brevicomin, and (±)-3,4- dehydro-exo-brevicomin: Racemic pheromones with a 6,8-dioxabicyclo[3.2.1]octane ring

Protective group-free syntheses of four racemic pheromones with a 6,8-dioxabicyclo[3.2.1]octane ring were achieved in five or six steps from commercially available (±)-3-butyn-2-ol (6) and 2-alkenyl halides or 2-alken-1-ol by employing Lewis acid-catalyzed acetalization of δ, ε-epoxy ketones as the key reaction. (±)- Frontalin (1) was prepared in a 25% overall yield in five steps from methallyl chloride (5a), (±)-endo-brevicomin (2) was prepared in a 23% overall yield in five steps from (E)-2-pentenyl bromide (5b), and (±)-exo-brevicomin (3) and (±)-3,4-dehydro-exo-brevicomin (4) were both prepared in a 4%overall yield in six steps based on (Z)-2-penten-1-ol (12).

Pheromone synthesis, CXCVII. Synthesis of the enantiomers of 2-sec- butyl-4,5-dihydrothiazole and (1R,5S,7R)-3,4-dehydro-exo-brevicomin, pheromone components of the male mouse, Mus musculus

Two components [2-sec-butyl-4,5-dihydrothiazole (1) and 3,4-dehydro-exo- brevicomin (2)] of a male-produced pheromone of the mouse Mus musculus have been synthesized in optically active forms. The enantiomers of 1 were obtained with an enantiomeric purity of ca. 92% ee and were found to be readily racemizable. Asymmetric dihydroxylation was employed as the key reaction (15→16) allowing the preparation of (1R,5S,7R)-2 with ca. 94% ee.

Ready access to the 6,8-dioxabicyclo[3.2.1]octane ring system using asymmetric heterocycloaddition induced by a chiral sulfoxide: Application to the total synthesis of the Mus musculus pheromone

A new stereocontrolled total synthesis of the (1R,5S,7R)-exo-6,8- dioxabicyclo[3.2.1]oct-3-ene skeleton of the Mus musculus pheromone has been achieved via an asymmetric intermolecular Diels-Alder reaction and an intramolecular conjugated addition, contro

THE CARBONYL EPOXIDE REARRANGEMENT. A CHIRAL SYNTHESIS OF THE MUS MUSCULUS PHEROMONE

The carbonyl-epoxide rearrangement in conjunction with the Sharpless asymmetric epoxidation procedure has been applied to an efficient synthesis of both enantiomers corresponding to the Mus musculus pheromone.

SYNTHESIS OF BOTH THE ENANTIOMERS OF 7-ETHYL-5-METHYL-6,8-DIOXABICYCLOOCT-3-ENE, THE MUS MUSCULUS (HOUSE MOUSE) PHEROMONE

Both the enantiomers of the pheromone of the male mouse Mus musculus, exo-7-ethyl-5-methyl-6,8-dioxabicyclooct-3-ene, were synthesized from the enantiomers of tartaric acid.

APPLICATION OF THE CARBONYL EPOXIDE REARRANGEMENT TO THE FORMATION OF DIOXABICYCLOALKANES AND ALKENES. SYNTHESIS OF THE MUS MUSCULUS PHEROMONE

Acid-catalyzed intramolecular opening of epoxides by carbonyl groups provides a general stereocontrolled method for forming dioxabicyclo systems, including the (+/-)-Mus musculus pheromone and products corresponding to certain insect pheromones.

REMARKABLE STEREOCONTROL IN THE ADDITION OF AN ANION TO AN α-ALKOXYALDEHYDE BY ENCOURAGING OR DISCOURAGING INTERNAL COMPLEXATION. APPLICATION TO BRIEF SYNTHESES OF THE MUS MUSCULUS (HOUSE MOUSE) PHEROMONE AND EXO-BREVICOMIN.

Stereoselective addition of ethylmetallic reagents to acrolein dimer 1 and the conversion of the threo alcohol 4t to exo-brevicomin and the Mus musculus pheromone are reported.

Chelation-Controlled Facially Selective Cyclocondensation Reactions of Chiral Alkoxy Aldehydes: Syntheses of a Mouse Androgen and of a Carbon-Linked Disaccharide

Magnesium bromide in tetrahydrofuran catalyzes the cycloaddition of a variety of chiral alkoxy aldehydes with activated butadienes.The stereochemistry of these products is such that they can be rationalized as arising from a reacting conformer in which th