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Beilstein J. Org. Chem. 2017, 13, 1430–1438, doi:10.3762/bjoc.13.140
Graphical Abstract
Figure 1: Structure of fusaricidins E (1) and F (2).
Figure 2: NOESY /COSY and HMBC correlations of compound 1.
Figure 3: Fragmentation pattern of compounds 1 and 2.
Scheme 1: Retrosynthetic plan for the depsipeptide and GHPD side chain.
Scheme 2: a) LiAlH4, THF, reflux, 12 h, quant.; b) Fmoc-OSu, NaHCO3, 1,4-dioxane, H2O, 0 °C to rt, 87%; c) 1:...
Scheme 3: Ester bond formation with 2,2-dimethylated pseudoproline including peptide 16.
Scheme 4: Cyclization with 2,2-dimethylated pseudoproline including peptide 16.
Scheme 5: Depsipeptide cyclization and coupling with GHPD side chain.
Figure 4: Byproducts from removal of Cbz group in THF and DMF.
Beilstein J. Org. Chem. 2014, 10, 251–258, doi:10.3762/bjoc.10.20
Figure 1: HMBC, COSY and NOESY correlations of compound 1.
Figure 2: HMBC, COSY and NOESY correlations of compound 2.
Figure 3: HMBC, COSY and NOESY correlations of compound 3.
Figure 4: HMBC, COSY and NOESY correlations of compound 4.
Figure 5: Structures of the isolated compounds.
Figure 6: Crystal structures (ORTEP plot) of arohynapene A (5, left) and tanzawaic acid E (8, right). Thermal...