Total syntheses of the coumarin-containing natural products pimpinellin and fraxetin using Au(I)-catalyzed intramolecular hydroarylation (IMHA) chemistry

Aymeric Cervi; Paul Aillard; Nourallah Hazeri; Laurent Petit; Christina L.L. Chai; Anthony C. Willis; Martin G. Banwell

doi:10.1021/jo401583q

Total syntheses of the coumarin-containing natural products pimpinellin and fraxetin using Au(I)-catalyzed intramolecular hydroarylation (IMHA) chemistry

Aymeric Cervi, Paul Aillard, Nourallah Hazeri, Laurent Petit, Christina L.L. Chai, Anthony C. Willis, Martin G. Banwell^*

^*Corresponding author for this work

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

53 Citations (Scopus)

Abstract

The title natural products (1 and 2, respectively) have been synthesized by Au(I)-catalyzed intramolecular hydroarylation (IMHA) of the relevant aryl propiolate esters (e.g., 13), which were themselves formed by reaction of the corresponding phenols with either 3-(trimethylsilyl)propiolic acid or propiolic acid and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride or dicyclohexylcarbodiimide. (±)-Purpurasol (3) was readily derived from fraxetin (2) by established procedures.

Original language	English
Pages (from-to)	9876-9882
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	78
Issue number	19
DOIs	https://doi.org/10.1021/jo401583q
Publication status	Published - 4 Oct 2013

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title = "Total syntheses of the coumarin-containing natural products pimpinellin and fraxetin using Au(I)-catalyzed intramolecular hydroarylation (IMHA) chemistry",

abstract = "The title natural products (1 and 2, respectively) have been synthesized by Au(I)-catalyzed intramolecular hydroarylation (IMHA) of the relevant aryl propiolate esters (e.g., 13), which were themselves formed by reaction of the corresponding phenols with either 3-(trimethylsilyl)propiolic acid or propiolic acid and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride or dicyclohexylcarbodiimide. (±)-Purpurasol (3) was readily derived from fraxetin (2) by established procedures.",

author = "Aymeric Cervi and Paul Aillard and Nourallah Hazeri and Laurent Petit and Chai, \{Christina L.L.\} and Willis, \{Anthony C.\} and Banwell, \{Martin G.\}",

year = "2013",

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doi = "10.1021/jo401583q",

language = "English",

volume = "78",

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journal = "Journal of Organic Chemistry",

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T1 - Total syntheses of the coumarin-containing natural products pimpinellin and fraxetin using Au(I)-catalyzed intramolecular hydroarylation (IMHA) chemistry

AU - Cervi, Aymeric

AU - Aillard, Paul

AU - Hazeri, Nourallah

AU - Petit, Laurent

AU - Chai, Christina L.L.

AU - Willis, Anthony C.

AU - Banwell, Martin G.

PY - 2013/10/4

Y1 - 2013/10/4

N2 - The title natural products (1 and 2, respectively) have been synthesized by Au(I)-catalyzed intramolecular hydroarylation (IMHA) of the relevant aryl propiolate esters (e.g., 13), which were themselves formed by reaction of the corresponding phenols with either 3-(trimethylsilyl)propiolic acid or propiolic acid and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride or dicyclohexylcarbodiimide. (±)-Purpurasol (3) was readily derived from fraxetin (2) by established procedures.

AB - The title natural products (1 and 2, respectively) have been synthesized by Au(I)-catalyzed intramolecular hydroarylation (IMHA) of the relevant aryl propiolate esters (e.g., 13), which were themselves formed by reaction of the corresponding phenols with either 3-(trimethylsilyl)propiolic acid or propiolic acid and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride or dicyclohexylcarbodiimide. (±)-Purpurasol (3) was readily derived from fraxetin (2) by established procedures.

UR - https://www.scopus.com/pages/publications/84885129808

U2 - 10.1021/jo401583q

DO - 10.1021/jo401583q

M3 - Article

SN - 0022-3263

VL - 78

SP - 9876

EP - 9882

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -

Total syntheses of the coumarin-containing natural products pimpinellin and fraxetin using Au(I)-catalyzed intramolecular hydroarylation (IMHA) chemistry

Abstract

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