Literature DB >> 17165901

Enantioselective synthesis of nicotinic receptor probe 7,8-difluoro-1,2,3,4,5,6- hexahydro-1,5-methano-3-benzazocine.

Crystal G Bashore1, Michael G Vetelino, Michael C Wirtz, Paige R Brooks, Heather N Frost, Ruth E McDermott, David C Whritenour, John A Ragan, Jennifer L Rutherford, Teresa W Makowski, Steven J Brenek, Jotham W Coe.   

Abstract

[Structure: see text] The development of a concise enantioselective synthesis of nicotinic alkaloid 1 is presented. The route features the synthesis and use of a "stable" aliphatic triflate 21 in an alkylation step to generate Heck precursor 24 and an enantioselective cyclization to establish a compound with the key [3.2.1]-bicyclic core, 29.

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Year:  2006        PMID: 17165901     DOI: 10.1021/ol0623062

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


  4 in total

1.  Manganese(III)-mediated transformations of phloroglucinols: a formal oxidative [4 + 2] cycloaddition leading to bicyclo[2.2.2]octadiones.

Authors:  Branko Mitasev; John A Porco
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

2.  Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations.

Authors:  Alan R Burns; Amaël G E Madec; Darryl W Low; Iain D Roy; Hon Wai Lam
Journal:  Chem Sci       Date:  2015-04-30       Impact factor: 9.825

3.  Sodium Diisopropylamide-Mediated Dehydrohalogenations: Influence of Primary- and Secondary-Shell Solvation.

Authors:  Yun Ma; Russell F Algera; Ryan A Woltornist; David B Collum
Journal:  J Org Chem       Date:  2019-08-22       Impact factor: 4.354

4.  Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes.

Authors:  Zhenbo Yuan; Yuye Zeng; Ziwen Feng; Zhe Guan; Aijun Lin; Hequan Yao
Journal:  Nat Commun       Date:  2020-05-21       Impact factor: 14.919

  4 in total

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