93218-39-4

Upstream product

• 108-24-7 acetic anhydride 
• 86421-21-8 (4RS,6S,7S)-Serricornin 
• 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 
• 631918-27-9 (2R,4S,5S)-1-(tert-butyl(dimethyl)silyloxy)-5-hydroxy-2,4-dimethylheptane 
• 631918-22-4 (2R,4S,5RS)-1-(tert-butyl(dimethyl)silyloxy)-5-hydroxy-2,4-dimethylheptane 
• 117248-20-1 (3R,5S,6S)-6-Ethyl-3,5-dimethyltetrahydro-2H-pyran-2-on 
• 147782-80-7 (2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol 
• 147782-81-8 (2S,4R)-1-<(tert-Butyldimethylsilyl)oxy>-2,4-dimethylpentanal 
• 335060-49-6 (2S,4R)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2,4-dimethylpentyl acetate 
• 59983-36-7 (S)-1-(1-Ethylpropylidenamino)-2-methoxymethylpyrrolidin 
• 6061-13-8 (2S,3S)-3-methylaspartic acid 
• 86562-29-0 (2R,3R)-(-)-threo-3-methylaspartic acid 

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 

Relevant academic research and scientific papers

SYNTHESIS OF 6S,7S-ANHYDRO-SERRICORNINE.

Diastereoselective and enantioselective reduction of the β-ketoester 3 by yeast to 4 provided the chiral starting material for a synthesis of 4RS,6S,7S-serricornine, having the same configuration as the natural product.This material was converted into optically active and diastereomerically pure 6S,7S-anhydro-serricornine (2).

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.

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.

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.

A new synthesis of serricornin [(4s,6s,7s)-7-hydroxy-4,6-dimethyl-3-nonanone], the sex pheromone of the cigarette beetle

Serricornin, the sex pheromone of Lasioderma serricorne F, was synthesised in 7.6% overall yield starting from methyl (R)-3-hydroxypentanoate of microbial origin. Its (4R,6S,7S)-isomer was also synthesised.

Stereoselective Synthesis of Alcohols, XVIII. - Synthesis of (3S,4S)-4-Methyl-3-heptanol and of (5S,6S)-Anhydroserricornin

Yeast reduction of methyl tetrahydro-4-oxo-2H-thiopyran-3-carboxylate (5) led to the β-hydroxy ester 6 of 98percent diastereomeric and ca. 85percent enantiomeric purity. 6 was converted into enantiomerically pure anti-4-methyl-3-heptanol (4) and via the key intermediate 11 into enantiomerically pure anhydroserricornin (3).

ELECTROPHILIC LACTONIZATION AS A TOOL IN ACYCLIC STEREOCONTROL; SYNTHESIS OF SERRICORNIN

Several electrophilic lactonization procedures have been explored as a means of functionalizing olefinic carboxylic acids with relative asymmetric induction.Iodolactonization of δ,ε-unsaturated acids under conditions of thermodynamic control exhibits good

SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF SERRICORNIN

The absolute stereochemistry of serricornin (4,6-dimethyl-7-hydroxy-3-nonanone) was established as 4S, 6S, 7S by synthesizing both (4S, 6S, 7S)-isomer and its antipode.Only the natural enantiomer was bioactive.by

A STEREOSELECTIVE SYNTHESIS OF "NATURAL" (4S,6S,7S)-SERRICORNIN, THE SEX PHEROMONE OF CIGARETTE BEETLE, FROM LEVOGLUCOSENONE

The natural stereoisomer of serricornin was synthesized stereoselectively from levoglucosenone.This firmly established the absolute stereochemistry of serricornin to be 4S,6S,7S.A short synthesis of (-)-δ-multistriatin was also reported.