Terpenes in organic synthesis

Gamalevich, G. D.; Morozov, B. N.; Serebryakov, É. P.

doi:10.1007/bf01433762

Cited by 4 publications

(6 citation statements)

References 16 publications

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“…− MS (EI); m/z (%) 125 (5), 111 (61), 97 (8), 83 (20), 85 (25), 69 (100), 55 (64). − The 1 H NMR and 13 C NMR spectral data are similar to those reported in the literature 18…”

Section: Methodssupporting

confidence: 79%

“…55 °C/13 mbar) to give R ‐8 (8.43 g, 73%), 99% pure by GC. − [α] D 25 = −7.19 ( c = 23.6, CHCl 3 ), ref 18. [α] D 20 = −7.40 ( c = 2.16, CHCl 3 ).…”

Section: Methodsmentioning

confidence: 99%

“…103 °C/11 mbar) furnished the title alcohol SS ‐8 (2.55 g, 46% based on the amount of SS ‐8 present in S ‐8 ), > 99% pure by GC and with 97.2% ( S ) configuration at C‐2. − [α] D 25 = −2.41 ( c = 2.24, CHCl 3 ), ref 18. [α] D 20 = −7.32 ( c = 1.68, CHCl 3 ).…”

Section: Methodsmentioning

confidence: 99%

“…B.p 100 °C/10 mbar. − [α] D 25 = −2.71 ( c = 2.65, CHCl 3 ), ref 18. [α] D 20 = −7.32 ( c = 1.68, CHCl 3 ).…”

Section: Methodsmentioning

confidence: 99%

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Syntheses of the Sixteen Stereoisomers of 3,7,11-Trimethyl-2-tridecanol, Including the (2S,3S,7S,11R) and (2S,3S,7S,11S) Stereoisomers Identified as Pheromone Precursors in Females of the Pine SawflyMicrodiprion pallipes(Hymenoptera: Diprionidae)

et al. 2001

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All sixteen stereoisomers of 3,7,11‐trimethyl‐2‐tridecanol were synthesised in high stereoisomerical purities (> 95%), for use in the identification of the stereoisomers present in females of the pine sawfly Microdiprion pallipes (Fallén) (Hymenoptera: Diprionidae) as the precursor of the actual sex pheromone (which is the propionate), and also for investigation of the biological activities of the esters. The key step in the syntheses was the coupling of each of the enantiomers of cis‐3,4‐dimethyl‐γ‐butyrolactone with each of the four pure stereoisomers of 1‐lithio‐2,6‐dimethyloctanes. The four corresponding alcohols were obtained by lipase‐catalysed (Amano PS) kinetic separation, based on selective acylation of either (2R/S,6S)‐ or (2R/S,6R)‐2,6‐dimethyl‐1‐octanol (obtained from the optically pure enantiomers of citronellal). Additionally, a mixture of the 16 possible stereoisomers of 3,7,11‐trimethyl‐2‐tridecanol was also prepared.

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“…− MS (EI); m/z (%) 125 (5), 111 (61), 97 (8), 83 (20), 85 (25), 69 (100), 55 (64). − The 1 H NMR and 13 C NMR spectral data are similar to those reported in the literature 18…”

Section: Methodssupporting

confidence: 79%

“…55 °C/13 mbar) to give R ‐8 (8.43 g, 73%), 99% pure by GC. − [α] D 25 = −7.19 ( c = 23.6, CHCl 3 ), ref 18. [α] D 20 = −7.40 ( c = 2.16, CHCl 3 ).…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…B.p 100 °C/10 mbar. − [α] D 25 = −2.71 ( c = 2.65, CHCl 3 ), ref 18. [α] D 20 = −7.32 ( c = 1.68, CHCl 3 ).…”

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Syntheses of the Sixteen Stereoisomers of 3,7,11-Trimethyl-2-tridecanol, Including the (2S,3S,7S,11R) and (2S,3S,7S,11S) Stereoisomers Identified as Pheromone Precursors in Females of the Pine SawflyMicrodiprion pallipes(Hymenoptera: Diprionidae)

et al. 2001

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“…Gamalevich et al studied the chemoenzymatic approach to the synthesis of all the stereoisomers of 1,6-dimethyloct-1-yl formate [100] and 2,6-dimethyloct-1-yl formate [101], pheromones of the smaller flour beetle. The key step involved enantioselective hydrolysis with porcine pancreatic lipase.…”

Section: Synthesis Of Hydroxylated Phero-mones and Related Compoundsmentioning

confidence: 99%

Biocatalysis Applied to the Synthesis of Pheromones

Aleu¹,

Bustillo²,

Hernández-Galán³

et al. 2007

COC

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The application of biologically derived catalysts to the synthesis of agrochemicals has become increasingly popular in recent years. In most cases, the aim of using a biotransformation is either to introduce chirality into the molecule, to achieve a regioselective functionalization, or to selectively convert a functional group among other groups with similar reactivity. Pheromones, which have recently been commercialized as agrochemicals, are generally used in enantiopure forms with their intentional mixtures. Since they are usually highly effective, only very small quantities are needed to achieve the desired activity. This review, with approximately 200 references covering the period previous to December 2004, describes various efficient means of preparing optically pure pheromones and their precursors with the aid of isolated enzymes and microorganisms serving as catalysts.

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