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Beilstein J. Org. Chem. 2015, 11, 265–270, doi:10.3762/bjoc.11.29
Graphical Abstract
Figure 1: Hyperaspidinols A (1) and B (2) and other compounds 3-6 from Hypericum chinense.
Figure 2: Hyperaspidinol A (1), target compound 7 and proposed precursors.
Scheme 1: Reagents and conditions: (i) triethylphosphonoacetate, DBU, THF, 48 h, 94%; (ii) H2, 10% Pd/C, EtOA...
Scheme 2: Reagents and conditions: (i) H3C(CH3O)NH·HCl, n-BuLi, THF, −78 °C, 4 h, 81%; (ii) 1-bromo-3,4-methy...
Figure 3: NOESY correlations in isomers 7a and 7b.
Figure 4: 3D representation of 7a.
Figure 5: 3D representation of 7b.
Figure 6: Possible mechanism for the formation of furo[2,3-b]chromenes 7a and 7b.