Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin

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

doi:10.1039/b918179b

Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin

Junxiu Meng, Tao Jiang, Huma Aslam Bhatti, Bina S. Siddiqui, Sally Dixon^*, Jeremy Dunbar Kilburn

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

36 Citations (Scopus)

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.

Original language	English
Pages (from-to)	107-113
Number of pages	7
Journal	Organic & Biomolecular Chemistry
Volume	8
Issue number	1
DOIs	https://doi.org/10.1039/b918179b
Publication status	Published - 2010

Keywords

C-H INSERTION
DIHYDROBENZOFURAN LIGNANS
BIOLOGICAL EVALUATION
CONIFERYL ALCOHOL
NEOLIGNANS
CONSTITUENTS
OXIDATION
POLYMERIZATION
BIOSYNTHESIS
INTERMEDIATE

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title = "Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin",

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.",

keywords = "C-H INSERTION, DIHYDROBENZOFURAN LIGNANS, BIOLOGICAL EVALUATION, CONIFERYL ALCOHOL, NEOLIGNANS, CONSTITUENTS, OXIDATION, POLYMERIZATION, BIOSYNTHESIS, INTERMEDIATE",

author = "Junxiu Meng and Tao Jiang and Bhatti, {Huma Aslam} and Siddiqui, {Bina S.} and Sally Dixon and Kilburn, {Jeremy Dunbar}",

year = "2010",

doi = "10.1039/b918179b",

language = "English",

volume = "8",

pages = "107--113",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0520",

publisher = "The Royal Society of Chemistry",

number = "1",

}

TY - JOUR

T1 - Synthesis of dihydrodehydrodiconiferyl alcohol

T2 - the revised structure of lawsonicin

AU - Meng, Junxiu

AU - Jiang, Tao

AU - Bhatti, Huma Aslam

AU - Siddiqui, Bina S.

AU - Dixon, Sally

AU - Kilburn, Jeremy Dunbar

PY - 2010

Y1 - 2010

N2 - 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.

AB - 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.

KW - C-H INSERTION

KW - DIHYDROBENZOFURAN LIGNANS

KW - BIOLOGICAL EVALUATION

KW - CONIFERYL ALCOHOL

KW - NEOLIGNANS

KW - CONSTITUENTS

KW - OXIDATION

KW - POLYMERIZATION

KW - BIOSYNTHESIS

KW - INTERMEDIATE

U2 - 10.1039/b918179b

DO - 10.1039/b918179b

M3 - Article

SN - 1477-0520

VL - 8

SP - 107

EP - 113

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 1

ER -

Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin

Abstract

Keywords

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