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Beilstein J. Org. Chem. 2016, 12, 2523–2534, doi:10.3762/bjoc.12.247
Graphical Abstract
Figure 1: Structures of (±)-naringenin, (±)-dracocephins A1–A4 and B1–B4 with the indication of the absolute ...
Scheme 1: Proposed biosynthetic route to dracocephins A and B.
Scheme 2: Synthesis of (±)-5-ethoxypyrrolidine-2-one ((±)-9).
Scheme 3: Synthesis of (±)-dracocephins A and B (±)-2a–d and (±)-3a–d and the elution order of stereoisomers ...
Figure 2: a) Chiral HPLC–UV and HPLC–ECD traces of dracocephins A (2a–d) using Chiralpak IC column with the e...
Figure 3: Structure and population of the low-energy CAM-B3LYP/TZVP PCM/CHCl3 conformers (>2%) of (R)-1.
Figure 4: Experimental HPLC–ECD spectrum of (R)-naringenin ((R)-1) compared with the Boltzmann-weighted ECD s...
Figure 5: Structure and population of the low-energy CAM-B3LYP/TZVP PCM/MeCN conformers (>2%) of (2R,5’’R)-2d....
Figure 6: Structure and population of the low-energy CAM-B3LYP/TZVP PCM/MeCN conformers (>2%) of (2R,5’’S)-2a....
Figure 7: Experimental HPLC-ECD spectra of (2R,5’’S)-2a (second eluted stereoisomer) and (2R,5’’R)-2d (fourth...
Figure 8: Experimental HPLC–ECD spectra of (2R,5’’S)-2a and (2R,5’’R)-2d compared with the Boltzmann-weighted...
Figure 9: a) Chiral HPLC–UV and HPLC–ECD traces of dracocephins B1–B4 3a–d using a Chiralpak IC column with t...
Figure 10: Structure and population of the low-energy CAM-B3LYP/TZVP PCM/MeCN conformers (>2%) of (2R,5’’R)-3c....
Figure 11: Structure and population of the low-energy CAM-B3LYP/TZVP PCM/MeCN conformers (>2%) of (2R,5’’S)-3b....
Figure 12: Experimental HPLC-ECD spectra of 3b (first eluted stereoisomer) and 3c (third eluted stereoisomer) ...
Figure 13: Experimental HPLC-ECD spectra of 3b and 3c compared with the Boltzmann-weighted ECD spectra compute...
Figure 14: Proposed mechanism for the formation of dracocephins A and B (2a–d and 3a–d) starting from (±)-9.