Synthesis of the Enantiomers of 2-sec-Butyl-4,5-dihydrothiazole and (1R,5S,7R)-3,4-Dehydro-exo-brevicomin, Pheromone Components of the Male Mouse,Mus musculus

Abstract

Two components [2‐sec‐butyl‐4,5‐dihydrothiazole (1) and 3,4‐dehydro‐exo‐brevicomin (2)] of a male‐produced pheromone of the mouse Musmusculus have been synthesized in optically active forms. The enantiomers of 1 were obtained with an enantiomeric purity of ca. 92% ee and were found to be readily racemizable. Asymmetric dihydroxylation was employed as the key reaction (15→16) allowing the preparation of (1R,5S,7R)‐2 with ca. 94% ee.

Semiochemical responsive olfactory sensory neurons are sexually dimorphic and plastic

“…The final product showed high purity by gas chromatography, 1 H and 13 C NMR, and mass spectroscopic data. The data were in agreement with reported parameters for this compound ( Tashiro and Mori, 1999 ). DHB was synthesized as previously described ( Wiesler et al, 1984 ).…”

Semiochemical responsive olfactory sensory neurons are sexually dimorphic and plastic

“…Racemic SBT was synthesized in two steps from 2-aminoethanol and methyl 2-methylbutanedithioate 44 in >80% yield according to the procedure of Abrunhosa et al 2001 45 . The final product showed high purity by gas chromatography, 1 H and 13 C NMR, and mass spectroscopic data; excellent agreement with reported parameters for this compound in Tashiro et al 1999 46 . DHB was synthesized as previously described in Wiesler et al 1984 47 .…”

Total synthesis and stereochemical assignment of bipolamide A acetate

“…The known oxazolidinone 17a 8 was subjected to asymmetric ethylation 9 using Evan's protocol to access the corresponding ethylated product exclusively which was treated further with LiBH 4 to get the known alcohol 18a . 10 Notably, the adopted protocol was found to be more efficient when compared to the Evan's methylation strategy 11 where a 4 : 1 diastereoselectivity was observed. Alcohol 18a was then oxidized using TPAP/NMO followed by Wittig olefination using Ph 3 PC(CH 3 )CO 2 Et to obtain the corresponding α,β-unsaturated E -olefin exclusively which further was reacted with DIBAL-H to yield allylic alcohol 19a .…”