Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin

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

doi:10.1039/B918179B

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Organic & Biomolecular Chemistry

Issue 1, 2010

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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

Org. Biomol. Chem., 2010, 8, 107-113

DOI: 10.1039/B918179B
Received 03 Sep 2009, Accepted 29 Sep 2009
First published on the web 28 Oct 2009

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Abstract
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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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¹³C NMR spectra for compounds 2, 8, 10–14, 16–20 and the isolated natural product
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Junxiu Meng
Tao Jiang
Huma Aslam Bhatti
Bina S. Siddiqui
Sally Dixon
Jeremy D. Kilburn

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Organic & Biomolecular Chemistry

Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin

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