New stereospecific syntheses of pheromone bombykol and its three geometrical isomers

Miyaura, Norio; Suginome, Hiroshi; Suzuki, Akira

doi:10.1016/s0040-4020(01)91575-3

Cited by 71 publications

(31 citation statements)

References 21 publications

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“…(E,Z)-10,12-hexadecadien-1-ol (bombykol) was synthesized stereospecifically starting from 1-pentyne (Sigma-Aldrich) and 10-undecyn-1-ol (Tokyo Kasei, Tokyo) following the protocol described (18). Distillation gave pure bombykol, and the stereochemistry was confirmed by the 1 H-NMR spectrum at 300 MHz.…”

Section: Methodsmentioning

confidence: 99%

Identification and functional characterization of a sex pheromone receptor in the silkmoth Bombyx mori

Sakurai

Nakagawa

Mitsuno

et al. 2004

Proc. Natl. Acad. Sci. U.S.A.

364

313

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Sex pheromones released by female moths are detected with high specificity and sensitivity in the olfactory sensilla of antennae of conspecific males. Bombykol in the silkmoth Bombyx mori was the first sex pheromone to be identified. Here we identify a malespecific G protein-coupled olfactory receptor gene, B. mori olfactory receptor 1 (BmOR-1), that appears to encode a bombykol receptor. The BmOR-1 gene is located on the Z sex chromosome, has an eight-exon͞seven-intron structure, and exhibits malespecific expression in the pheromone receptor neurons of male moth antenna during late pupal and adult stages. Bombykol stimulation of Xenopus laevis oocytes expressing BmOR-1 and BmG␣q elicited robust dose-dependent inward currents on twoelectrode voltage clamp recordings, demonstrating that the binding of bombykol to BmOR-1 leads to the activation of a BmG␣q-mediated signaling cascade. Antennae of female moths infected with BmOR-1-recombinant baculovirus showed electrophysiological responses to bombykol but not to bombykal. These results provide evidence that BmOR-1 is a G protein-coupled sex pheromone receptor that recognizes bombykol.baculovirus ͉ bombykal ͉ bombykol ͉ olfactory receptor ͉ Xenopus laevis oocyte

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Section: Methodsmentioning

confidence: 99%

Identification and functional characterization of a sex pheromone receptor in the silkmoth Bombyx mori

Sakurai

Nakagawa

Mitsuno

et al. 2004

Proc. Natl. Acad. Sci. U.S.A.

364

313

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“…Alcohol 8 was also synthesized by Suginome and co-workers using 11-hydroxy-1-uncenyl boronic acid as a key intermediate. 12 The yield of this synthesis (38% in 5 steps) was little bit higher than ours (34% in 5 steps), however, the experimental procedure of our synthesis was simpler than that of the reported synthesis. Oxidation of the primary alcohol 8 with SO3 ・ pyridine and DMSO afforded aldehyde 9.…”

Section: Resultsmentioning

confidence: 53%

Synthesis of both enantiomers of akolactone B and (+)-ancepsenolide

Hikosaka

Hattori

Makabe

2014

Tetrahedron: Asymmetry

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“…The Suzuki reaction provides access to all four stereoisomers, as an (E)-or (Z)-1-alkenylboronic acid may be linked to an (E)-or (Z)-configured vinyl halide (14). While we could not constantly obtain very high yields, the stereoselectivity of the reaction was always excellent.…”

Section: Resultsmentioning

confidence: 84%

“…Yield: 5.6 g (74%). MS Preparation of (Z)-1-(2′-tetrahydropyranyloxy)-octadec-10-yn-12-ene (14). (Z)-1-Bromo-1-heptene (11) (0.71 g, 4 mmol), 76 mg copper(I) iodide (0.4 mmol), 76 mg bis(benzonitrile)-dichloropalladium(II) (PdCl 2 [PhCN] 2 , 0.2 mmol), and 12 mL piperidine were placed in a 25-mL dry flask.…”

Section: Methodsmentioning

confidence: 99%