Issue 1, 2010
From the journal:

Organic & Biomolecular Chemistry

Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin†

Junxiu Meng,ab   Tao Jiang,b   Huma Aslam Bhatti,c   Bina S. Siddiqui,c   Sally Dixon*a  and  Jeremy D. Kilburn*a  

* Corresponding authors

a School of Chemistry, University of Southampton, Southampton, UK
E-mail: sd5@soton.ac.uk, jdk1@soton.ac.uk
Fax: +44(23)80594182
Tel: +44(23)80593596

b Key Laboratory of Marine Drugs, Ministry of Education of China, School of Pharmacy, Ocean University of China, Qingdao, China

c H.E.J Research Institute of Chemistry, International Centre for Chemical Sciences, University of Karachi, Karachi-75270, Pakistan

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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Article information

DOI
https://doi.org/10.1039/B918179B
Article type
Paper
Submitted
03 Sep 2009
Accepted
29 Sep 2009
First published
28 Oct 2009

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

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Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin

J. Meng, T. Jiang, H. Aslam Bhatti, B. S. Siddiqui, S. Dixon and J. D. Kilburn, Org. Biomol. Chem., 2010, 8, 107 DOI: 10.1039/B918179B

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