| Structure Identification: |
| Chemical & pharmaceutical bulletin 43(11), 2014-2018, 1995-11-15 | | Studies on the Chemical Constituents of Xanthoxylum nitidum (ROXB.)D. C. (Fagara nitida ROXB.). III. The Chemical Constituents of the Wood[Reference: WebLink] | The chemical constituents of the wood of Xanthoxylum nitidum (ROXB.) D. C.(Fagara nitida ROXB.) were examined.
METHODS AND RESULTS:
Two phenylpropanoids, methyl nitinoate (2) and dihydrocuspidiol (3), and a benzodioxane type lignan, Nitidanin (4), were newly isolated. The structures of the phenylpropanoids were chemically determined. In addition, the application of a selective insensitive nuclei enhanced by polarization transfer selective (INEPT) technique in the NMR spectrum to the new lignan allowed us to deduce the structure. | | Cheminform, 2007, 38(20):771-4. | | Total synthesis of (±)-nitidanin and novel procedures for determination of the location of the side chains on 1,4-benzodioxane[Reference: WebLink] |
METHODS AND RESULTS:
Regioselective cycloaddition of o-quinone 4 and protected sinapyl alcohol 2 gave 1,4-benzodioxane 5, which was converted to (±)-Nitidanin (6), an antimalarial compound.
CONCLUSIONS:
Two novel procedures were developed to determine the location of the side chains of the adduct (5) based on partial ring cleavage. |
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