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Beilstein J. Org. Chem. 2013, 9, 2925–2933, doi:10.3762/bjoc.9.329
Graphical Abstract
Figure 1: (−)-(5R,6Z)-Dendrolasin-5-acetate (1), its 6E derivative and naturally occuring dentrolasin (3).
Figure 2: Selected HMBC, COSY, and nOe correlations of 1.
Scheme 1: Synthetic route to sesquiterpene 1.
Scheme 2: Mechanism of Wittig rearrangement [21].
Figure 3: (a) NP HPLC trace showing separation of racemic 5-hydroxydendrolasin (7a/b) using hexanes/EtOAc (90...
Figure 4: Analytical enantioselective HPLC trace showing separation of individual enantiomers of (6Z)-5-hydro...
Figure 5: The 1H NMR (CDCl3, 500 MHz) spectroscopic comparison of (6Z)-dendrolasin-5-acetate (1): (a) sample ...
Figure 6: RP HPLC trace showing separation of the MPA esters (R,R)-11 and (R,S)-11 (MeCN/H2O, 63:35 over 50 m...
Figure 7: Enantioselective HPLC profiles (5% isopropanol in n-hexane) of 1: (a) synthetic (±) mixture; (b) sy...