Literature DB >> 17362042

General strategy for the construction of enantiopure pyrrolidine-based alkaloids. Total synthesis of (-)-monomorine.

Suhong Zhang1, Liang Xu, Lei Miao, Hong Shu, Mark L Trudell.   

Abstract

An enantiopure cis-2,5-disubstituted pyrrolidine building block was prepared from cocaine. The synthetic utility of this compound as a chiral building block was demonstrated by a short and efficient synthesis of the pyrrolidine-based alkaloid (-)-monomorine (six steps, 37% overall yield).

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Year:  2007        PMID： 17362042     DOI： 10.1021/jo062532p

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


  5 in total

1.  Enantioselective syntheses of both enantiomers of cis-pyrrolidine 225H.

Authors:  Hong Shu; April R Noble; Suhong Zhang; Lei Miao; Mark L Trudell
Journal:  Tetrahedron       Date:  2010-06       Impact factor: 2.457

2.  Stereoselective synthesis of cis-2,5-disubstituted pyrrolidines via Wacker-type aerobic oxidative cyclization of alkenes with tert-butanesulfinamide nucleophiles.

Authors:  Joanne E Redford; Richard I McDonald; Matthew L Rigsby; Joshua D Wiensch; Shannon S Stahl
Journal:  Org Lett       Date:  2012-02-21       Impact factor: 6.005

Review 3.  Applications of alkyl orthoesters as valuable substrates in organic transformations, focusing on reaction media.

Authors:  Zahra Khademi; Kobra Nikoofar
Journal:  RSC Adv       Date:  2020-08-17       Impact factor: 4.036

4.  Catalytic Asymmetric Synthesis of Chiral γ-Amino Ketones via Umpolung Reactions of Imines.

Authors:  Lin Hu; Yongwei Wu; Zhe Li; Li Deng
Journal:  J Am Chem Soc       Date:  2016-11-30       Impact factor: 15.419

5.  A regio- and stereoselective ω-transaminase/monoamine oxidase cascade for the synthesis of chiral 2,5-disubstituted pyrrolidines.

Authors:  Elaine O'Reilly; Cesar Iglesias; Diego Ghislieri; Jennifer Hopwood; James L Galman; Richard C Lloyd; Nicholas J Turner
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-29       Impact factor: 15.336
  5 in total

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