Paper

Org. Biomol. Chem., 2010, 8, 107 - 113, DOI: 10.1039/b918179b

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Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin

Junxiu Meng, Tao Jiang, Huma Aslam Bhatti, Bina S. Siddiqui, Sally Dixon and Jeremy D. Kilburn

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Structural revision of lawsonicin, a natural product of Lawsonia alba, is reported based upon comparison of its spectral data with that of the naturally occurring dihydrobenzo[b]furan neolignan (rac)-trans-dihydrodehydrodiconiferyl alcohol, which is found to be identical. A concise synthesis of dihydrodehydrodiconiferyl alcohol, via Rh₂[S-DOSP]₄-catalysed intramolecular C–H insertion, is described.

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