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- W2171918360 abstract "Abstract (S)-β-Bisabolene, (S)-1, was synthetized by a synthetic route in which (S)-4-methyl-3-cyclohexene carboxylic acid, (S)-10, which was the key intermediate, was prepared via a highly diastereoselective TiCl4-catalyzed Diels-Alder reaction between isoprene and the acrylate of commercial (R)-pantolactone, followed by hydrolysis. Compound (S)-10 was then converted into ketone (S)-13 using two different procedures. The best one of these, as regards the degree of stereospecificity, involved the reaction of (S)-10 with 2 equiv of 4-methyl-3-penten-1-yllithium, 14, in the presence of CeCl3, and gave (S)-13 having ca. 84% ee. The Zr-promoted methylenation of this ketone afforded highly enantiomerically enriched (S)-1." @default.
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- W2171918360 date "1995-10-01" @default.
- W2171918360 modified "2023-10-03" @default.
- W2171918360 title "Asymmetric Synthesis of Highly Enantiomerically Enriched (<i>S</i>)(-)-β-Bisabolene" @default.
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- W2171918360 doi "https://doi.org/10.1080/00397919508011421" @default.
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