Protecting group free syntheses of (±)-columbianetin and (±)-angelmarin

Eric B.J. Harris; Martin G. Banwell; Anthony C. Willis

doi:10.1016/j.tetlet.2011.10.036

Protecting group free syntheses of (±)-columbianetin and (±)-angelmarin

Eric B.J. Harris, Martin G. Banwell^*, Anthony C. Willis

^*Corresponding author for this work

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

23 Citations (Scopus)

Abstract

A five-step and protecting group free synthesis of (±)-columbianetin from cyclohexane-1,3-dione is reported. The former compound was converted into its p-hydroxycinnamate derivative, (±)-angelmarin, using Coster's esterification procedure. Efforts to modify the synthesis so as to prepare angelmarin and columbianetin in an enantioselective manner are described.

Original language	English
Pages (from-to)	6887-6889
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	51
DOIs	https://doi.org/10.1016/j.tetlet.2011.10.036
Publication status	Published - 21 Dec 2011

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10.1016/j.tetlet.2011.10.036

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title = "Protecting group free syntheses of (±)-columbianetin and (±)-angelmarin",

abstract = "A five-step and protecting group free synthesis of (±)-columbianetin from cyclohexane-1,3-dione is reported. The former compound was converted into its p-hydroxycinnamate derivative, (±)-angelmarin, using Coster's esterification procedure. Efforts to modify the synthesis so as to prepare angelmarin and columbianetin in an enantioselective manner are described.",

keywords = "Angelmarin, Aromatization, Columbianetin, Coumarin, Intramolecular hydroarylation",

author = "Harris, {Eric B.J.} and Banwell, {Martin G.} and Willis, {Anthony C.}",

year = "2011",

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T1 - Protecting group free syntheses of (±)-columbianetin and (±)-angelmarin

AU - Harris, Eric B.J.

AU - Banwell, Martin G.

AU - Willis, Anthony C.

PY - 2011/12/21

Y1 - 2011/12/21

N2 - A five-step and protecting group free synthesis of (±)-columbianetin from cyclohexane-1,3-dione is reported. The former compound was converted into its p-hydroxycinnamate derivative, (±)-angelmarin, using Coster's esterification procedure. Efforts to modify the synthesis so as to prepare angelmarin and columbianetin in an enantioselective manner are described.

AB - A five-step and protecting group free synthesis of (±)-columbianetin from cyclohexane-1,3-dione is reported. The former compound was converted into its p-hydroxycinnamate derivative, (±)-angelmarin, using Coster's esterification procedure. Efforts to modify the synthesis so as to prepare angelmarin and columbianetin in an enantioselective manner are described.

KW - Angelmarin

KW - Aromatization

KW - Columbianetin

KW - Coumarin

KW - Intramolecular hydroarylation

UR - http://www.scopus.com/inward/record.url?scp=81255129274&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2011.10.036

DO - 10.1016/j.tetlet.2011.10.036

M3 - Article

SN - 0040-4039

VL - 52

SP - 6887

EP - 6889

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 51

ER -

Protecting group free syntheses of (±)-columbianetin and (±)-angelmarin

Abstract

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