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Literature DB >> 17078698

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.

Vincent Rodeschini¹, Nadia M Ahmad, Nigel S Simpkins.

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.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 17078698 DOI： 10.1021/ol0620592

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

6 in total

1. Total synthesis of (±)-7-epi-nemorosone.

Authors: Qiang Zhang; John A Porco
Journal: Org Lett Date: 2012-03-26 Impact factor: 6.005

2. The total synthesis of hyperpapuanone, hyperibone L, epi-clusianone and oblongifolin A.

Authors: Nicole Biber; Katrin Möws; Bernd Plietker
Journal: Nat Chem Date: 2011-10-16 Impact factor: 24.427

3. Asymmetric total synthesis of (+)- and (-)-clusianone and (+)- and (-)-clusianone methyl enol ether via ACC alkylation and evaluation of their anti-HIV activity.

Authors: Michelle R Garnsey; James A Matous; Jesse J Kwiek; Don M Coltart
Journal: Bioorg Med Chem Lett Date: 2011-02-23 Impact factor: 2.823

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.

1. Total synthesis of (±)-7-epi-nemorosone.

2. The total synthesis of hyperpapuanone, hyperibone L, epi-clusianone and oblongifolin A.

3. Asymmetric total synthesis of (+)- and (-)-clusianone and (+)- and (-)-clusianone methyl enol ether via ACC alkylation and evaluation of their anti-HIV activity.

4. Asymmetric, stereodivergent synthesis of (-)-clusianone utilizing a biomimetic cationic cyclization.

5. Synthetic Efforts Toward [3.3.1] Bridged Bicyclic Phloroglucinol Natural Products.

6. Programmable meroterpene synthesis.