Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin

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 dihy...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2010-01, Vol.8 (1), p.107-113
Main Authors: Meng, Junxiu, Jiang, Tao, Aslam Bhatti, Huma, Siddiqui, Bina S, Dixon, Sally, Kilburn, Jeremy D
Format: Article
Language:English
Subjects:
Lawsonia Plant - chemistry
Lignin - analogs & derivatives
Lignin - chemical synthesis
Lignin - chemistry
Molecular Structure
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Summary: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 Rh(2)[S-DOSP](4)-catalysed intramolecular C-H insertion, is described.
ISSN:1477-0520
1477-0539
DOI:10.1039/b918179b