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Beilstein J. Org. Chem. 2019, 15, 2184–2190, doi:10.3762/bjoc.15.215
Graphical Abstract
Scheme 1: Mechanism of the ADS-catalysed conversion of FDP (2) to amorpha-4,11-diene (3), a biosynthetic prec...
Scheme 2: Synthesis of 8-methoxy-FDP (11) and 12-methoxy-FDP (12) (for full synthesis details see Supporting Information File 1).
Figure 1: Total-ion chromatogram of the pentane extractable products formed in an incubation of ADS with 8-me...
Figure 2: 1H NMR spectrum (500 MHz, CDCl3) of the 8-methoxy-γ-humulene (20) generated by ADS from 8-methoxy-F...
Scheme 3: Potential mechanisms for the ADS-catalysed conversion of 8-methoxy-FDP (11) to 8-methoxy-γ-humulene...
Figure 3: Total-ion chromatogram of the pentane extractable products formed in an incubation of ADS with 12-m...
Figure 4: 1H NMR spectrum (400 MHz, CDCl3) of 12-methoxy-β-sesquiphellandrene (26) and 12-methoxyzingiberene (...
Scheme 4: Possible mechanisms for the ADS-catalysed conversion of 12-methoxy-FDP (12) to 12-methoxy-β-sesquip...