Synthesis of the Enantiomers ofanti-2,6-Dimethylheptane-1,7-diol Monotetrahydropyranyl Ether and Their Conversion into the Enantiomers of the Sex Pheromone Components of the Apple Leafminer,Lyonetia prunifoliella

Abstract

Both (2R,6R)‐ and (2S,6S)‐isomers of 2,6‐dimethylheptane‐1,7‐diol monotetrahydropyranyl ether (4) were synthesized, and converted into the enantiomers of anti‐10,14‐dimethyl‐1‐octadecene (1), anti‐5,9‐dimethyloctadecane (2) and anti‐5,9‐dimethylheptadecane (3), the sex pheromone components of the apple leafminer (Lyonetia prunifoliella).

Asymmetric synthesis of the sex pheromone of the apple leafminer, Lyonetia prunifoliella

“…The final hydrogenation reduction gave the desired pheromones 2 and 3 in 88–95% yield 37 . Their chemical data were in accord with the previous synthesis 11 …”

“…31 To remove the olefinic byproduct, we treated the mixture with m-CPBA and afforded the desired pheromone 1 (21% yield two steps). 11 Its NMR spectra and specific rotation were matched the reference. 12 Having achieved the preparation of pheromone 1, we explored the synthesis of pheromones 2 and 3 (Scheme 4).…”

“…The silica gel column chromatography (DCM/npentane 1:1) provided (S)-3-methylheptan-1-ol ( 13 C NMR data for this compound are consistence with the literature data. 14 2.8 | Synthesis of (S)-3-methylheptanal (11) According to the similar manner of aldehyde 8, the oxidation of (S)-3-methylheptan-1-ol (10) 2.9 | Synthesis of (S)-4-benzyl-3-(undec-10-enoyl)oxazolidin-2-one (13) According to the similar manner of oxazolidinone amide 5, the acylation of undec-10-enoic acid ( 2.12 | Synthesis of (S)-11-bromo-10-methylundec-1-ene ( 16)…”

Ternatin and improved synthetic variants kill cancer cells by targeting the elongation factor-1A ternary complex

“…as described ( MacKinnon et al, 2007 ). (2 R ,3 R )-ethyl 2-amino-3-hydroxy-4-methylpentanoate ( Shimokawa et al, 2007 ) ( 11 , Figure 8 ), tripeptide 17 ( Figure 8 ) ( Shimokawa et al, 2009 ), and iodides 6a and 6b ( Nakamura and Mori, 2000 ; Smith et al, 1996 ) were prepared as described.…”

Enantiospecific synthesis and filed evaluation of four stereoisomers of 10,14-dimethyloctadec-1-ene, a sex pheromone component secreted by female moths of the apple leafminer

“…The anion of methyl phenyl sulfone is easily reacted with a primary alkyl halide and usually used as a one-carbon linchpin. 10) It is noteworthy that the anion attached to a chiral secondary tosylate in this study and created a methyl branch with exact stereochemistry. The two chiral blocks (S)-7 and (S)-9 were coupled by using BuLi as a base in THF-HMPA to give (10S,13SR,14S)-10 with a 10,14-dimethyl skeleton.…”