99427-16-4

Upstream product

• 1564-98-3 (3R)-5-(3,3-dimethyloxiran-2-yl)-3-methylpentan-1-ol 
• 18951-85-4 (R)-citronellic acid 
• 1117-61-9 (3R)-citronellol 
• 79517-78-5 (R)-(+)-6-acetoxy-4-methylhexanal 
• 20425-54-1 (R)-1-citronellyl acetate 
• 82425-91-0 (R)-(+)-6-Hydroxy-3-methylhexyl acetate 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1070-32-2 (R)-(+)-3-Methyl-1-heptanol 
• 99493-42-2 (S)-(+)-14-Methyl-1-octadecene 
• 99582-18-0 (R)-3-Methyl-15-hexadecenyl tosylate 
• 99427-19-7 (R)-3-Methylheptyl tosylate 

Relevant academic research and scientific papers

Pheromone synthesis, CXCII. - Synthesis of all the stereoisomers of 10,14-dimethyloctadec-1-ene, 5,9-dimethyloctadecane and 5,9- dimethylheptadecane, the sex pheromone components of the apple leafminer, Lyonetia prunifoliella

All of the stereoisomers of 10,14-dimethyloctadec-1-ene (1), 5,9- dimethyloctadecane (2) and 5,9-dimethylheptadecane (3), the sex pheromone components of the apple leafminer (Lyonetia prunifoliella), were synthesized by starting from the enantiomers of ci

ENANTIO-CONTROLLED SYNTHESIS OF THE MACROCYCLIC C14-C23 SUBUNIT OF CYTOCHALASIN B

The synthesis of the C14-C23 macrocyclic subunit of cytochalasin B from pulegone is described.The key feature of this synthesis is the photo-induced rearrangement of epoxy diazomethyl ketone E to a γ-hydroxy alkenoic ester (Scheme 2).The intermediate epoxy alcohol F was prepared using the asymmetric Sharpless epoxidation.Considerable attention was given to the preparation of allylic alcohol 14, having a t-butyldimethylsilyloxy protecting function, as starting material for the asymmetric epoxidation, however, several unforeseen difficulties were encountered (Schemes 3 and 4).Satisfactory results were obtained using the methoxy group as protecting function (Scheme 5).The allylic alcohol 22 was prepared from bromide 20 by chain lengthening with propargyl alcohol.The Sharpless epoxidation of 22 took place with high induction.Conversion to epoxy ester 24, to diazo ketone 25 and photo-rearrangement to 26 and deprotection to give 28, completes the sequence.

Pheromone Syntheses, LXXVII. - New Synthesis of the Enantiomers of 14-Methyl-1-octadecene, the Pheromone of Lyonetia clerkella L.

The synthesis of the title compounds (R)-1 and (S)-1 from (R)-citronellic acid (R)-2 is described.