83997-86-8

Upstream product

• 108-24-7 acetic anhydride 
• 86421-21-8 (4RS,6S,7S)-Serricornin 
• 84230-97-7 (2R,3S)-3-(tert-Butyldimethylsiloxy)-1-iod-2-methylpentan 
• 78433-62-2 (4RS,6S,7S)-7-t-butyldimethylsilyloxy-4,6-dimethyl-3-nonanone 
• 90276-94-1 (3R,4S)-Tetrahydro-4-hydroxy-2H-thiopyran-3-carbonsaeure 
• 84230-94-4 (3R,4S)-Tetrahydro-4-hydroxy-2H-thiopyran-3-carbonsaeure-methylester 
• 72598-35-7 (-)-serricornin 
• 82290-64-0 Acetic acid (1S,2S,4S)-1-ethyl-4-(2-ethyl-[1,3]dithian-2-yl)-2-methyl-pentyl ester 
• 72522-40-8 (4R,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone 
• 59983-36-7 (S)-1-(1-Ethylpropylidenamino)-2-methoxymethylpyrrolidin 
• 13398-41-9 (2S, 3S)-threo-β-methylmalic acid 
• 77333-42-7 (2S,3R)-threo-3-methylbutane-1,2,4-triol 
• 69743-60-8 (2S,3R)-threo-3-methylbutane-1,2,4-triol 1,2-acetonide 
• 100235-81-2 methyl (2R,3R)-2-methyl-3-tetrahydropyranyloxypentenoate 

Downstream Products

• 72485-37-1 (4R^*,6S^*,7S^*)-7-acetyloxy-4,6-dimethyl-3-nonanone 
• 72485-37-1 (4R^*,6R^*,7R^*)-7-acetyloxy-4,6-dimethyl-3-nonanone 
• 72598-35-7 (-)-serricornin 

Relevant academic research and scientific papers

STEREOSELECTIVE SYNTHESIS OF NATURAL (4S,6S,7S)-SERRICORNIN STARTING WITH (3S,4S)-4-HYDROXY-3-METHYL-1-HEXENE

(4S,6S,7S)-Serricornin has been synthesized in three steps starting with (3S,4S)-4-hydroxy-3-methyl-1-hexene.

Synthesis of (4R,6S,7R)-7-hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5-dimethyl-2-octanone

The synthesis of (4R,6S,7R)-7-hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5-dimethyl-2-octanone is described as their acetates using a desymmetrization strategy as well as an Evans syn aldol strategy.

Thiopyran route to polypropionates: An efficient synthesis of serricornin

The synthesis of serricornin [(4S,6S,7S)-7-hydroxy-4,6-dimethylnonan-3-one] , a sex pheromone produced by the female cigarette beetle (Lasioderma serricorne F.), in seven steps from readily available racemic 1,4-dioxa-8-thiaspiro-[4.5] decane-6-carboxaldehyde (6) is described. The key steps include enantioselective aldol reaction of 6 with tetrahydrothiopyran-4-one catalyzed by 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole to fabricate the tetrapropionate skeleton, stereoselective LisBu3BH reduction of the resulting aldol adduct, Barton-McCombie deoxygenation, and Raney nickel desulfurization.

Synthesis of a biologically active analog of the sex pheromone of cigarette beetle (Lasioderma serricorne)

A simple synthesis of a diastereomeric mixture of 7-hydroxy-4,6- dimethylnonan-3-ones was carried out. In the biological action, it is an analog of serricornin, the sex pheromone of the cigarette beetle (Lasioderma serricorne).

Synthesis of (4R,6S,7R)-7-hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5-dimethyl-2-octanone, the pheromone components of the bostrychid beetle, Dinoderus bifoveolatus

(4R,6S,7R)-7-Hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5- dimethyl-2-octanone, the pheromone components of the bostrychid beetle, Dinoderus bifoveolatus, as well as their (4R,6S,7S)-and (3R,5S,6S)-isomers were synthesized from (2R,4S,5R)- and (2R,4S,5S)2,4-dimethyl-5-heptanolide, respectively.

New synthesis of serricornin, the sex pheromone of the cigarette beetle (Lasioderma serricorne)

A new approach to the total synthesis of serricornin, the sex pheromone of the cigarette beetle, based on readily available (4S,5E)-4-methyhept-5-enenitrile was implemented.

New synthesis of serricornin, the female sex pheromone of the cigarette beetle

Serricornin [(4S,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone], the female sex pheromone of Lasioderma serricorne, was synthesized by starting from (2S,4S)-2,4-dimethyl-1,5-pentanediol that had been obtained by lipase-catalyzed enantiomer separation of its racemate.

The baker's yeast reduction of the β-keto aldehydes in the presence of a sulfur compound

Improved enantio- and diastereoselectivity was achieved in the baker's yeast reduction of β-keto aldehyde derivatives using a sulfur compound as an additive. The resulting enantiomerically pure diol was transformed into serricornin, a sex pheromone of the cigarette beetle.

Enantioselective Synthesis of (-)-Serricornin, a Sex Pheromone of a Female Cigarette Beetle (Lasioderma serricorne F.)

(-)-Serricornin, a sex pheromone of a cigarette beetle (Lasioderma serricorne F.), has been synthesized highly stereoselectively starting from (Z)-4-benzyloxy-2-buten-1-ol by employing the Katsuki-Sharpless asymmetric epoxidation and two stereospecific me

AN EFFICIENT AND STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-SERRICORNINE

An efficient and stereoselective total synthesis of (+/-)-serricornine (1) the sex pheromone produced by the female cigarette beetle Lasioderma serricorne F, is described. (3SR,5SR,6SR)-6-Ethyltetrahydro-3,5-dimethyl-2H-pyran-2-one (10) is prepared in 65percent yield through lactonization of a 1:1 mixture of C-2 epimrs of the corresponding esters.