Literature DB >> 20725594

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

Hong Shu1, April R Noble, Suhong Zhang, Lei Miao, Mark L Trudell.   

Abstract

The efficient and expeditious syntheses of both enantiomers of the amphibian alkaloid cis-225H have been achieved. Utilizing a common cis-2,5-disubstituted pyrrolidine building block derived from (+)-2-tropinone, the enantioselective syntheses have established the absolute configuration of these alkaloids as (+)-(2R,5S) and (-)-(5S,2R).

Entities:  

Year:  2010        PMID: 20725594      PMCID: PMC2922008          DOI: 10.1016/j.tet.2010.04.037

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  18 in total

1.  Stereoselective synthesis of pyrrolidines from N-allyl oxazolidines via hydrozirconation-cyclization.

Authors:  Jean-Luc Vasse; Antoine Joosten; Clément Denhez; Jan Szymoniak
Journal:  Org Lett       Date:  2005-10-27       Impact factor: 6.005

2.  Venom chemistry of the ant Myrmicaria melanogaster from Brunei.

Authors:  Tappey H Jones; Heather L Voegtle; Heather M Miras; Robert G Weatherford; Thomas F Spande; H Martin Garraffo; John W Daly; Diane W Davidson; Roy R Snelling
Journal:  J Nat Prod       Date:  2007-01-23       Impact factor: 4.050

3.  2,5-Disubstituted pyrrolidines: synthesis by enamine reduction and subsequent regioselective and diastereoselective alkylations.

Authors:  Syed Raziullah Hussaini; Mark G Moloney
Journal:  Org Biomol Chem       Date:  2006-05-31       Impact factor: 3.876

4.  Chemistry of venom alkaloids in the antMegalomyrmex foreli (Myrmicinae) from Costa Rica.

Authors:  T H Jones; P J Devries; P Escoubas
Journal:  J Chem Ecol       Date:  1991-12       Impact factor: 2.626

5.  Alkaloids from dendrobatid frogs: structures of two omega-hydroxy congeners of 3-butyl-5-propylindolizidine and occurrence of 2,5-disubstituted pyrrolidines and a 2,6-disubstituted piperidine.

Authors:  J W Daly; T F Spande; N Whittaker; R J Highet; D Feigl; N Nishimori; T Tokuyama; C W Myers
Journal:  J Nat Prod       Date:  1986 Mar-Apr       Impact factor: 4.050

Review 6.  Indolizidine and quinolizidine alkaloids.

Authors:  Joseph P Michael
Journal:  Nat Prod Rep       Date:  2004-09-14       Impact factor: 13.423

7.  An uptake system for dietary alkaloids in poison frogs (Dendrobatidae).

Authors:  J W Daly; S I Secunda; H M Garraffo; T F Spande; A Wisnieski; J F Cover
Journal:  Toxicon       Date:  1994-06       Impact factor: 3.033

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

Authors:  Suhong Zhang; Liang Xu; Lei Miao; Hong Shu; Mark L Trudell
Journal:  J Org Chem       Date:  2007-03-16       Impact factor: 4.354

9.  The venom alkaloids from some African Monomorium species.

Authors:  T H Jones; V E Zottig; H G Robertson; R R Snelling
Journal:  J Chem Ecol       Date:  2003-12       Impact factor: 2.626

10.  Asymmetric synthesis of trans-2,5-disubstituted pyrrolidines from enantiopure homoallylic amines. Synthesis of pyrrolidine (-)-197B.

Authors:  Franklin A Davis; Minsoo Song; Alexander Augustine
Journal:  J Org Chem       Date:  2006-03-31       Impact factor: 4.354

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