Literature DB >> 17628069

Double conjugate addition of a nitropropionate ester to a quinone monoketal: synthesis of an advanced intermediate to (+/-)-gelsemine.

Scott Grecian1, Jeffrey Aubé.   

Abstract

A double conjugate addition between the lithium dianion of ethyl 3-nitropropionate and p-benzoquinone dimethyl ketal afforded a mixture of diastereomeric [3.2.1]bicylooctanones. These products were converted into an advanced intermediate previously carried forward to (+/-)-gelsemine by Fukuyama and Liu.

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Year:  2007        PMID： 17628069      PMCID： PMC2518665          DOI： 10.1021/ol071174p

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


  6 in total

1.  Enantioselective Total Synthesis of (+)-Gelsemine: Determination of Its Absolute Configuration This work was supported in part by the Ministry of Education, Sports, and Culture, Japan. S.Y. thanks the JSPS for a predoctoral fellowship.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-11-17       Impact factor: 15.336

2.  Use of the intramolecular Heck reaction for forming congested quaternary carbon stereocenters. Stereocontrolled total synthesis of (+/-)-gelsemine.

Authors:  Andrew Madin; Christopher J O'Donnell; Taeboem Oh; David W Old; Larry E Overman; Matthew J Sharp
Journal:  J Am Chem Soc       Date:  2005-12-28       Impact factor: 15.419

3.  Total Synthesis of (+/-)-Gelsemine.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-10-04       Impact factor: 15.336

4.  Regioselective single and double conjugate additions to substituted cyclohexa-2,5-dienone monoacetals.

Authors:  Scott Grecian; Aaron D Wrobleski; Jeffrey Aubé
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

5.  Explorations in organic chemistry leading to the total synthesis of (+/-)-gelsemine.

Authors:  Fay W Ng; Hong Lin; Pauline Chiu; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2002-08-21       Impact factor: 15.419

Review 6.  Gelsemine: a thought-provoking target for total synthesis.

Authors:  Hong Lin; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2003-01-03       Impact factor: 15.336
  6 in total
  2 in total

1.  Synthesis of o-chlorophenols via an unexpected nucleophilic chlorination of quinone monoketals mediated by N,N'-dimethylhydrazine dihydrochloride.

Authors:  Zhiwei Yin; Jinzhu Zhang; Jing Wu; Riana Green; Sihan Li; Shengping Zheng
Journal:  Org Biomol Chem       Date:  2014-05-14       Impact factor: 3.876

2.  Total synthesis of (+)-gelsemine via an organocatalytic Diels-Alder approach.

Authors:  Xiaoming Chen; Shengguo Duan; Cheng Tao; Hongbin Zhai; Fayang G Qiu
Journal:  Nat Commun       Date:  2015-05-21       Impact factor: 14.919
  2 in total

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