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Literature DB >> 17465570

Kinetic resolution in a bridgehead lithiation mediated by a chiral bis-lithium amide: assignment of the absolute configuration of clusianone.

Vincent Rodeschini¹, Nigel S Simpkins, Claire Wilson.

Abstract

A chiral base kinetic resolution of an advanced bicyclic intermediate enabled access to the polyprenylated phloroglucinol natural product (+)-clusianone in enantiomerically pure form. X-ray structure determination of another product obtained by the same method then allowed the absolute stereochemistry of (+)-clusianone to be assigned.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17465570 DOI： 10.1021/jo070225t

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

6 in total

1. Rapid access to polyprenylated phloroglucinols via alkylative dearomatization-annulation: total synthesis of (+/-)-clusianone(1).

Authors: Ji Qi; John A Porco
Journal: J Am Chem Soc Date: 2007-09-29 Impact factor: 15.419

2. 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

3. Catalytic enantioselective alkylative dearomatization-annulation: total synthesis and absolute configuration assignment of hyperibone K.

Authors: Ji Qi; Aaron B Beeler; Qiang Zhang; John A Porco
Journal: J Am Chem Soc Date: 2010-10-06 Impact factor: 15.419

Kinetic resolution in a bridgehead lithiation mediated by a chiral bis-lithium amide: assignment of the absolute configuration of clusianone.

1. Rapid access to polyprenylated phloroglucinols via alkylative dearomatization-annulation: total synthesis of (+/-)-clusianone(1).

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

3. Catalytic enantioselective alkylative dearomatization-annulation: total synthesis and absolute configuration assignment of hyperibone K.

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

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

6. Stereopermutation on the Putative Structure of the Marine Natural Product Mucosin.