Literature DB >> 18443655

Application of an intramolecular dipolar cycloaddition to an asymmetric synthesis of the fully oxygenated tricyclic core of the stemofoline alkaloids.

Ryan J Carra1, Matthew T Epperson, David Y Gin.   

Abstract

An intramolecular non-stabilized azomethine ylide dipolar cycloaddition was applied toward the first non-racemic synthesis of the fully-oxygenated bridged pyrrolizidine core (45) of (+)-stemofoline (1) in eleven steps from a commercially available starting material.

Entities:  

Year:  2008        PMID： 18443655      PMCID： PMC2352155          DOI： 10.1016/j.tet.2008.02.008

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


  11 in total

1.  Asymmetric 1,3-Dipolar Cycloaddition Reactions.

Authors:  Kurt V. Gothelf; Karl Anker Jørgensen
Journal:  Chem Rev       Date:  1998-04-02       Impact factor: 60.622

2.  Feeding deterrence and contact toxicity of Stemona alkaloids-a source of potent natural insecticides.

Authors:  Brigitte Brem; Christoph Seger; Thomas Pacher; Otmar Hofer; Srunya Vajrodaya; Harald Greger
Journal:  J Agric Food Chem       Date:  2002-10-23       Impact factor: 5.279

3.  Phytochemical studies on Stemona plants: isolation of stemofoline alkaloids.

Authors:  Thanapat Sastraruji; Araya Jatisatienr; Stephen G Pyne; Alison T Ung; Wilford Lie; Morwenna C Williams
Journal:  J Nat Prod       Date:  2005-12       Impact factor: 4.050

4.  Intramolecular dipolar cycloaddition reactions of azomethine ylides.

Authors:  Iain Coldham; Richard Hufton
Journal:  Chem Rev       Date:  2005-07       Impact factor: 60.622

5.  Two pyrrolo[1,2-a]azepine type alkaloids from Stemona collinsae Craib: structure elucidations, relationship to asparagamine A, and a new biogenetic concept of their formation.

Authors:  Christoph Seger; Kurt Mereiter; Elisabeth Kaltenegger; Thomas Pacher; Harald Greger; Otmar Hofer
Journal:  Chem Biodivers       Date:  2004-02       Impact factor: 2.408

6.  Phytochemical studies on Stemona burkillii prain: two new dihydrostemofoline alkaloids.

Authors:  Pitchaya Mungkornasawakul; Stephen G Pyne; Araya Jatisatienr; Wilford Lie; Alison T Ung; Kritchaya Issakul; Auntika Sawatwanich; Damrat Supyen; Chaiwat Jatisatienr
Journal:  J Nat Prod       Date:  2004-10       Impact factor: 4.050

7.  Synthetic approaches to the polycyclic alkaloid stemofoline.

Authors:  Alison M Baylis; Michael P H Davies; Eric J Thomas
Journal:  Org Biomol Chem       Date:  2007-08-14       Impact factor: 3.876

8.  Total synthesis of (+/-)-didehydrostemofoline (asparagamine A) and (+/-)-isodidehydrostemofoline.

Authors:  Markus Brüggemann; Andrew I McDonald; Larry E Overman; Mark D Rosen; Lothar Schwink; Jeremy P Scott
Journal:  J Am Chem Soc       Date:  2003-12-17       Impact factor: 15.419

9.  Insecticidal pyrido[1,2-a]azepine alkaloids and related derivatives from Stemona species.

Authors:  Elisabeth Kaltenegger; Brigitte Brem; Kurt Mereiter; Hermann Kalchhauser; Hanspeter Kählig; Otmar Hofer; Srumya Vajrodaya; Harald Greger
Journal:  Phytochemistry       Date:  2003-08       Impact factor: 4.072

10.  Enantiospecific synthesis of the bridged pyrrolizidine core of asparagamine A: dipolar cycloadditions of azomethine ylides derived from the sulfonylation of vinylogous amides.

Authors:  Matthew T Epperson; David Y Gin
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336
View more
  5 in total

1.  Novel Entry to the Tricyclic Core of Stemofoline and Didehydrostemofoline.

Authors:  Jochen Dietz; Stephen F Martin
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

2.  New Regio- and Stereoselective Cascades via Unstabilized Azomethine Ylide Cycloadditions for the Synthesis of Highly Substituted Tropane and Indolizidine Frameworks.

Authors:  Shuming Chen; Vlad Bacauanu; Tobias Knecht; Brandon Q Mercado; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2016-09-19       Impact factor: 15.419

3.  Toward a total synthesis of the stemofoline alkaloids: Advancement of a 1,3-dipolar cycloaddition strategy.

Authors:  Charles S Shanahan; Nathan O Fuller; Bjoern Ludolph; Stephen F Martin
Journal:  Tetrahedron Lett       Date:  2011-08-10       Impact factor: 2.415

4.  Asymmetric Formal Total Synthesis of the Stemofoline Alkaloids: The Evolution, Development and Application of a Catalytic Dipolar Cycloaddition Cascade.

Authors:  Charles S Shanahan; Chao Fang; Daniel H Paull; Stephen F Martin
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

5.  Enantioselective formal total syntheses of didehydrostemofoline and isodidehydrostemofoline through a catalytic dipolar cycloaddition cascade.

Authors:  Chao Fang; Charles S Shanahan; Daniel H Paull; Stephen F Martin
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-17       Impact factor: 15.336
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.