Stereoselective synthesis of an alarm pheromone of Grematogaster ants using (4S)-4-benzyloxazolidinone as chiral auxiliary

Zhou, Fang; Lu, Cuifen; Chen, Z. X.; Yang, Guichun

doi:10.1007/s10600-010-9531-7

Cited by 7 publications

(2 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…(R)-28 and (S)-69 were synthesized using similar reactions. 86,209 Furthermore, a-methyl secondary alcohols (44)(45)(46) were synthesized by asymmetric aldol condensation using an imide of another chiral oxazolidinone (R-1-4e). 137 The boron enolate derivative from the imide was treated with n-pentanal or n-butanal to afford syn adducts.…”

Section: Application Of Stereoselective Reactionsmentioning

confidence: 99%

Chiral methyl-branched pheromones

Ando

Yamakawa

2015

Nat. Prod. Rep.

View full text Add to dashboard Cite

Insect pheromones are some of the most interesting natural products because they are utilized for interspecific communication between various insects, such as beetles, moths, ants, and cockroaches. A large number of compounds of many kinds have been identified as pheromone components, reflecting the diversity of insect species. While this review deals only with chiral methyl-branched pheromones, the chemical structures of more than one hundred non-terpene compounds have been determined by applying excellent analytical techniques. Furthermore, their stereoselective syntheses have been achieved by employing trustworthy chiral sources and ingenious enantioselective reactions. The information has been reviewed here not only to make them available for new research but also to understand the characteristic chemical structures of the chiral pheromones. Since biosynthetic studies are still limited, it might be meaningful to examine whether the structures, particularly the positions and configurations of the branched methyl groups, are correlated with the taxonomy of the pheromone producers and also with the function of the pheromones in communication systems.

show abstract

Section: Application Of Stereoselective Reactionsmentioning

confidence: 99%

Chiral methyl-branched pheromones

Ando

Yamakawa

2015

Nat. Prod. Rep.

View full text Add to dashboard Cite

show abstract

“…Several syntheses of this compound as the racemate and an enantiomer are known [2][3][4][5][6]. However, many of them involve several steps and most are labor-intensive and require costly starting materials.…”

Section: Dzhemilevmentioning

confidence: 99%

One-Step Synthesis of Racemic 6-Methyloctan-3-One, an Alarm Pheromone Component of Ants of the Genus Crematogaster

2015

View full text Add to dashboard Cite

Dzhemilev6-Methyloctan-3-one (1) was identified as a component of the alarm pheromone of ants of the genus Crematogaster [1]. Several syntheses of this compound as the racemate and an enantiomer are known [2][3][4][5][6]. However, many of them involve several steps and most are labor-intensive and require costly starting materials.We developed a convenient and effective synthetic pathway for a racemic analog of 1 that was based on our recently proposed regioselective carbonylation of 1-alkenes using Et 2 Zn and TaCl 5 catalyst [7].The reaction of but-1-ene with Et 2 Zn in the presence of TaCl 5 (Et 2 Zn-but-1-ene-TaCl 5 = 110:100:5; Et 2 Zn concentration 1.0 mmol/mL in hexane, 20°C, 5 h) formed organozinc compound 2. For this, hexane (20 mL) was cooled to -15°C and treated with but-1-ene (2.25 ml, 20 mmol) cooled to -30°C. Then, the solution was cooled to -15-20°C, treated with Et 2 Zn (2.25 mL, 22 mmol) and TaCl 5 (0.4 g, 1 mmol), heated gradually to room temperature, stirred for 5 h, cooled to -5°C, and treated dropwise with propionylchloride (3, 1.74 mL, 20 mmol) in hexane. All these operations were performed under a dry Ar atmosphere. The resulting reaction mixture was stirred for 2 h and treated with aqueous HCl solution (10%). The resulting 1 was extracted by Et 2 O (3 u 50 mL). The extracts were dried over anhydrous MgSO 4 . The solvent was distilled off. The residue was chromatographed (SiO 2 , hexane) to afford 1 (2.69 g, 99% pure) in 95% yield based on 3 (Scheme 1).The structure of 1 was proven using IR, PMR, and 13 C NMR spectral methods and GC-MS in addition to comparison with an authentic sample [6]. REFERENCES 1.R. M. Crewe, M. S. Blum, and C. A. Collingwood, Comp.

show abstract

Carboxy‐Directed Asymmetric Hydrogenation of 1,1‐Diarylethenes and 1,1‐Dialkylethenes

Song

Zhu

et al. 2012

Angewandte Chemie

View full text Add to dashboard Cite

Stereoselective synthesis of an alarm pheromone of Grematogaster ants using (4S)-4-benzyloxazolidinone as chiral auxiliary

Cited by 7 publications

References 10 publications

Chiral methyl-branched pheromones

Chiral methyl-branched pheromones

One-Step Synthesis of Racemic 6-Methyloctan-3-One, an Alarm Pheromone Component of Ants of the Genus Crematogaster

Carboxy‐Directed Asymmetric Hydrogenation of 1,1‐Diarylethenes and 1,1‐Dialkylethenes

Contact Info

Product

Resources

About