Literature DB >> 10841495

Regiocontrol in an intramolecular Schmidt reaction: total synthesis of (+)-aspidospermidine.

R Iyengar1, K Schildknegt, J Aubé.   

Abstract

[reaction--see text] A total synthesis of (+)-aspidospermidine (1) is described, featuring an intramolecular Schmidt reaction as the key step. The effects of stereochemistry and protecting group status on the regio- and chemoselectivity of this reaction were examined.

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Year:  2000        PMID： 10841495     DOI： 10.1021/ol005913c

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


  13 in total

1.  Au-catalyzed synthesis of 2-alkylindoles from N-arylhydroxylamines and terminal alkynes.

Authors:  Yanzhao Wang; Longwu Ye; Liming Zhang
Journal:  Chem Commun (Camb)       Date:  2011-06-03       Impact factor: 6.222

2.  Cation-pi control of regiochemistry of intramolecular schmidt reactions en route to bridged bicyclic lactams.

Authors:  Lei Yao; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2007-02-16       Impact factor: 15.419

Review 3.  Chemistry of bridged lactams and related heterocycles.

Authors:  Michal Szostak; Jeffrey Aubé
Journal:  Chem Rev       Date:  2013-06-17       Impact factor: 60.622

4.  Application of the Rh(II) cyclization/cycloaddition cascade for the total synthesis of (+/-)-aspidophytine.

Authors:  José M Mejía-Oneto; Albert Padwa
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

5.  A FISCHER INDOLIZATION STRATEGY TOWARD THE TOTAL SYNTHESIS OF (-)-GONIOMITINE.

Authors:  Beau P Pritchett; Jun Kikuchi; Yoshitaka Numajiri; Brian M Stoltz
Journal:  Heterocycles       Date:  2017-02-15       Impact factor: 0.831

6.  Formal synthesis of aspidosperma alkaloids via the intramolecular [3 + 2] cycloaddition of 2-azapentdienyllithiums.

Authors:  William H Pearson; Aaron Aponick
Journal:  Org Lett       Date:  2006-04-13       Impact factor: 6.005

7.  Revisiting a classic approach to the Aspidosperma alkaloids: an intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine.

Authors:  Rajesh Iyengar; Klaas Schildknegt; Martha Morton; Jeffrey Aubé
Journal:  J Org Chem       Date:  2005-12-23       Impact factor: 4.354

8.  A Dipolar Cycloaddition Approach Toward the Kopsifoline Alkaloid Framework.

Authors:  Xuechuan Hong; Stefan France; Albert Padwa
Journal:  Tetrahedron       Date:  2007-06-25       Impact factor: 2.457

9.  Overcoming product inhibition in catalysis of the intramolecular Schmidt reaction.

Authors:  Hashim F Motiwala; Charlie Fehl; Sze-Wan Li; Erin Hirt; Patrick Porubsky; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2013-06-07       Impact factor: 15.419

10.  Concise and enantioselective total synthesis of (-)-mehranine, (-)-methylenebismehranine, and related Aspidosperma alkaloids.

Authors:  Marius Mewald; Jonathan William Medley; Mohammad Movassaghi
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-04       Impact factor: 15.336
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