1983
DOI: 10.1021/jf00115a035
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Conversion of (S)-allethrolone to pyrethrin I, jasmolin I, cinerin I, and [propenyl-3-13C]- and [propenyl-3-14C]-(S)-bioallethrin

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Cited by 6 publications
(7 citation statements)
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References 10 publications
(16 reference statements)
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“…( S )- 12 : Pale yellow oil; [ α ] D 17 + 33.7 ( c 1.39, CHCl 3 ) [lit . [ α ] D 23 + 29.2 ( c 1.7, CHCl 3 )].…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…( S )- 12 : Pale yellow oil; [ α ] D 17 + 33.7 ( c 1.39, CHCl 3 ) [lit . [ α ] D 23 + 29.2 ( c 1.7, CHCl 3 )].…”
Section: Methodsmentioning
confidence: 99%
“…Because of the structural resemblance of pyrethrin families, practical separation of pure ingredients from the natural mixture products is virtually impossible, even using recent elaborate techniques. In 1983, Casida and Ando disclosed the first synthetic approach and structure confirmation of “chiral” pyrethrin I based on the analytical data of 90 MHz 1 H NMR spectra and optical rotations . They used the starting ( S )-4-hydroxy-3-methyl-2-(allyl)­cyclopent-2-en-1-one precursor with unknown chemical and optical purities that was gifted from a certain company.…”
Section: Introductionmentioning
confidence: 99%
“…According to Todd et al (2003), pyrethrins are non-volatile at ambient temperatures (WHO, 1975), with low vapor pressures and low Henry's constants, and large octanol/water coefficients (Table 1). Synthesis of pyrethrin I, jasmolin I, and cinerin I from (S)-Allethrolone has been reported by Ando and Casida (1983).…”
Section: Chemical Propertiesmentioning
confidence: 99%
“…Interestingly, the elution order of the (Z)-and (E)-isomers in this HPLC system was different from that by GLC and Si0 2 -AgN0 3 column. 4 ) HPLC analyses for these mixtures were also examined with other polar columns (Nucleosil N0 2 and N(CH 3 )2) and another solvent system (2-propanol in n-hexane). Although the elution order was the same for every combination, the ability to separate the stereoisomers was different to various extents.…”
Section: 'Z)- (1s2'e)-and (1r2'e)-isomers Of Pyrethrin I ((A)-i)mentioning
confidence: 99%
“…4 ) This mixture, which gave only one spot· on a silica gel TLC plate, was analyzed on a Nuc1eosil 5CN HPLC column (8 mm i.d. x 20 cm) with 1% tetrahydrofuran (THF) in n-hexane.…”
mentioning
confidence: 99%