The chemistry of thujone. VII. Thujone as a chiral synthon for the preparation of sesquiterpenes. Synthesis of β-elemol

Abstract

An efficient synthesis of β-elemol (4) from thujone (1) is described. The key intermediate 3 is readily prepared and described in previous studies within the synthesis of (+)-carissone (2).

Insecticidal compounds from the essential oil of Chinese medicinal herb Atractylodes chinensis

“…13 C‐NMR: δ 150.2 (C‐7), 147.9 (C‐9), 112.1 (C‐11), 109.9 (C‐8), 72.7 (C‐12), 52.8 (C‐5), 49.4 (C‐3), 39.9 (C‐1), 39.7 (C‐15), 28.5 (C‐6), 27.2 (C‐4), 27.2 (C‐14), 24.8 (C‐13), 22.6 (C‐10), 16.6 (C‐2). The 1 H and 13 C NMR data were in agreement with reported data 21…”

Three-Component Synthesis of α,β-Cyclopropyl-γ-Amino Acids

“…Desilylation (TBAF/AcOH) afforded 76% and 96% of alcohols 5a and 5b . Unfortunately, after conversion to the intermediate selenide, oxidation and elimination afforded the desired vinyl cyclopropanes 6a and 6b in poor yields. However, a modification developed by Reich which involved oxidation of the intermediate selenide with m -CPBA at low temperature (−40 °C) followed by elimination in the presence of 5 equiv of diisopropylamine afforded these alkenes in excellent yields (82−88%, two steps).…”

Total Syntheses of Sesterpenic Acids: Refuted (±)-Bilosespenes A and B

“…11 Compound 13 was then transformed into 15 in excellent yield by hydrolysis of the ketal moiety and sodium periodate mediated oxidative-elimination. 12 Having successfully installed the requisite exo-methylene group, all that remained to complete the synthesis of the target molecule was to convert the carbonyl function into R,β-unsaturated acid moiety.…”

“…Conversion of the alcohol 12 into selenide 13 was performed using Grieco's method . Compound 13 was then transformed into 15 in excellent yield by hydrolysis of the ketal moiety and sodium periodate mediated oxidative-elimination …”