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Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin

Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin
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 dihydrodehydrodiconiferyl alcohol, via Rh(2)[S-DOSP](4)-catalysed intramolecular C-H insertion, is described.
1477-0520
107-113
Meng, Junxiu
4826e3e4-b519-4040-b4ab-98f24358f08a
Jiang, Tao
9e527cf6-43a9-46a5-845e-bc66c9ce15ac
Aslam Bhatti, Huma
72631036-4eec-4ef2-9f20-e7be8499a8c9
Siddiqui, Bina S.
544d0369-adce-4647-a217-06c76c37a7ff
Dixon, Sally
943160fc-1b70-4c29-b2e3-b7785cee8a0c
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a
Meng, Junxiu
4826e3e4-b519-4040-b4ab-98f24358f08a
Jiang, Tao
9e527cf6-43a9-46a5-845e-bc66c9ce15ac
Aslam Bhatti, Huma
72631036-4eec-4ef2-9f20-e7be8499a8c9
Siddiqui, Bina S.
544d0369-adce-4647-a217-06c76c37a7ff
Dixon, Sally
943160fc-1b70-4c29-b2e3-b7785cee8a0c
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a

Meng, Junxiu, Jiang, Tao, Aslam Bhatti, Huma, Siddiqui, Bina S., Dixon, Sally and Kilburn, Jeremy D. (2010) Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin. Organic & Biomolecular Chemistry, 8 (1), 107-113. (doi:10.1039/b918179b).

Record type: Article

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 Rh(2)[S-DOSP](4)-catalysed intramolecular C-H insertion, is described.

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Published date: January 2010

Identifiers

Local EPrints ID: 147097
URI: http://eprints.soton.ac.uk/id/eprint/147097
ISSN: 1477-0520
PURE UUID: f84242c9-b51f-4abd-893f-268c0fae2033
ORCID for Sally Dixon: ORCID iD orcid.org/0000-0003-2219-3635

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Date deposited: 23 Apr 2010 08:28
Last modified: 17 Dec 2019 01:51

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Contributors

Author: Junxiu Meng
Author: Tao Jiang
Author: Huma Aslam Bhatti
Author: Bina S. Siddiqui
Author: Sally Dixon ORCID iD
Author: Jeremy D. Kilburn

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