A synthesis of (+/-)-Clusianone: High-yielding Bridgehead and Diketone substitutions by Regioselective Lithiation of Enol Ether derivatives of Bicyclo[3.3.1]nonane-2,4,9-triones

V Rodeschini; NM Ahmad; Nigel Simpkins

doi:10.1021/ol0620592

A synthesis of (+/-)-Clusianone: High-yielding Bridgehead and Diketone substitutions by Regioselective Lithiation of Enol Ether derivatives of Bicyclo[3.3.1]nonane-2,4,9-triones

V Rodeschini
, NM Ahmad
, Nigel Simpkins

Chemistry

Research output: Contribution to journal › Article

62 Citations (Scopus)

Abstract

[Structure: see text] A concise synthesis of the polyprenylated acylphloroglucinol natural product, clusianone, in racemic form, is described. An Effenburger cyclization generated a core bicyclo[3.3.1]nonane-trione structure, which was then elaborated by means of regioselective lithiation reactions.

Original language	English
Pages (from-to)	5283-5285
Number of pages	3
Journal	Organic Letters
Volume	8
DOIs	https://doi.org/10.1021/ol0620592
Publication status	Published - 9 Nov 2006

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title = "A synthesis of (+/-)-Clusianone: High-yielding Bridgehead and Diketone substitutions by Regioselective Lithiation of Enol Ether derivatives of Bicyclo[3.3.1]nonane-2,4,9-triones",

abstract = "[Structure: see text] A concise synthesis of the polyprenylated acylphloroglucinol natural product, clusianone, in racemic form, is described. An Effenburger cyclization generated a core bicyclo[3.3.1]nonane-trione structure, which was then elaborated by means of regioselective lithiation reactions.",

author = "V Rodeschini and NM Ahmad and Nigel Simpkins",

year = "2006",

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doi = "10.1021/ol0620592",

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volume = "8",

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journal = "Organic Letters",

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T1 - A synthesis of (+/-)-Clusianone: High-yielding Bridgehead and Diketone substitutions by Regioselective Lithiation of Enol Ether derivatives of Bicyclo[3.3.1]nonane-2,4,9-triones

AU - Rodeschini, V

AU - Ahmad, NM

AU - Simpkins, Nigel

PY - 2006/11/9

Y1 - 2006/11/9

N2 - [Structure: see text] A concise synthesis of the polyprenylated acylphloroglucinol natural product, clusianone, in racemic form, is described. An Effenburger cyclization generated a core bicyclo[3.3.1]nonane-trione structure, which was then elaborated by means of regioselective lithiation reactions.

AB - [Structure: see text] A concise synthesis of the polyprenylated acylphloroglucinol natural product, clusianone, in racemic form, is described. An Effenburger cyclization generated a core bicyclo[3.3.1]nonane-trione structure, which was then elaborated by means of regioselective lithiation reactions.

U2 - 10.1021/ol0620592

DO - 10.1021/ol0620592

M3 - Article

C2 - 17078698

VL - 8

SP - 5283

EP - 5285

JO - Organic Letters

JF - Organic Letters

ER -

A synthesis of (+/-)-Clusianone: High-yielding Bridgehead and Diketone substitutions by Regioselective Lithiation of Enol Ether derivatives of Bicyclo[3.3.1]nonane-2,4,9-triones

Abstract

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