Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin?

Organic & Biomolecular Chemistry Pub Date: 2009-10-28 DOI: 10.1039/B918179B

Abstract

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.

Graphical abstract: Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin
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