83541-13-3

Upstream product

• 1117-61-9 (3R)-citronellol 
• 2385-77-5 (R)-Citronellal 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 83541-12-2 (R)-(+)-citronellyl benzyl ether 
• 96154-40-4 3,7-dimethyl-6-octenyl benzyl ether 

Downstream Products

• 86527-49-3 [(Z)-(R)-7-(1-Ethoxy-ethoxy)-3-methyl-non-6-en-8-ynyloxymethyl]-benzene 
• 1446944-89-3 (3R,11R)-3,11-dimethylpentadecyl tosylate 
• 146512-85-8 (3R)-1-benzyloxy-3-methyl-6-hexanol 
• 146512-86-9 (R)-6-benzyloxy-4-methylhexyl tosylate 
• 1446944-59-7 (R)-6-benzyloxy-4-methylhexyl iodide 
• 1446944-60-0 (R)-1-benzyloxy-3-methyl-7-pentadecyne 
• 89051-71-8 (R)-3-Methylpentadecyl tosylate 
• 1446944-74-6 (3R,11R)-1-benzyloxy-3,11,15-trimethyl-14-hexadecen-7-yne 
• 1446944-77-9 (3R,11R,14RS)-1-benzyloxy-14,15-epoxy-3,11,15-trimethyl-7-hexadecyne 
• 1446944-79-1 (3R,11S,14RS)-1-benzyloxy-14,15-epoxy-3,11,15-trimethyl-7-hexadecyne 
• 1446944-76-8 (3R,11S)-1-benzyloxy-3,11,15-trimethyl-14-hexadecen-7-yne 
• 1446944-80-4 (4S,12R)-14-benzyloxy-4,12-dimethyl-7-tetradecynal 
• 1446944-82-6 (4R,12R)-14-benzyloxy-4,12-dimethyl-7-tetradecynal 
• 1446944-83-7 (3R,11R)-1-benzyloxy-3,11-dimethyl-14-pentadecen-7-yne 

Relevant academic research and scientific papers

Pheromone synthesis. Part 256: Synthesis of the four stereoisomers of 5,11-dimethylpentacosane, a new sex pheromone component of the male Galleria mellonella (L.), with high stereochemical purities as determined by the derivatization-HPLC analysis of the eight stereoisomers of 5,11-dimethyl-8-pentacosanol

Abstract All the four stereoisomers of 5,11-dimethylpentacosane (>96.8% purity) were synthesized via the stereoisomers of 5,11-dimethyl-8-pentacosanol, whose stereoisomeric compositions could be determined precisely by their low temperature HPLC analysis after derivatization. 5,11-Dimethyl-8-pentacosanol was prepared by a Grignard reaction between 3-methylheptylmagnesium bromide and 4-methyloctadecanal, both of which were prepared from the commercially available enantiomers of citronellal (97-98% ee). Alternatively, (R)-3-methyl-1-heptanol could be prepared from methyl (R)-3-hydroxybutanoate (100% ee). Pd/C-catalyzed hydrogenation of a 5-methyl-1-alkene caused partial racemaization at C-5.

Synthesis of all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2-octadecanone, sex pheromone components of the Lyclene dharma dharma moth, from the enantiomers of citronellal

The enantiomers of citronellal were converted to all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2- octadecanone, the female-produced sex pheromone components of the Lyclene dharma dharma moth. Three wellestablished procedures, the Wittig reaction, alkylation of alkynes, and acetoacetic ester synthesis, were employed for the carbon-carbon bond formation to connect the building blocks.

Stereoselective synthesis of (-)-PF1163A via prins cyclization

A highly stereoselective and convergent total synthesis of PF1163 A is described while proving the versatility of Prins cyclization in natural product synthesis. The Prins cyclization, Yamaguchi esterification, and ring-closing metathesis reactions are th