Literature DB >> 16277507

An expeditious total synthesis of (+/-)-stenine.

Yibin Zeng1, Jeffrey Aubé.   

Abstract

(+/-)-Stenine was synthesized in eight steps from a known ketophosphonate reagent. The key step was an exo-selective Diels-Alder/intramolecular Schmidt domino reaction that afforded three of the four rings and four stereocenters in a single reaction.

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Year:  2005        PMID： 16277507     DOI： 10.1021/ja055629m

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  11 in total

Review 1.  Protecting-group-free synthesis as an opportunity for invention.

Authors:  Ian S Young; Phil S Baran
Journal:  Nat Chem       Date:  2009-06       Impact factor: 24.427

Review 2.  Chemistry of bridged lactams and related heterocycles.

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

3.  Synthesis and receptor profiling of Stemona alkaloid analogues reveal a potent class of sigma ligands.

Authors:  Kevin J Frankowski; Vincent Setola; Jon M Evans; Ben Neuenswander; Bryan L Roth; Jeffrey Aubé
Journal:  Proc Natl Acad Sci U S A       Date:  2011-02-28       Impact factor: 11.205

4.  Stereocontrol in a combined allylic azide rearrangement and intramolecular Schmidt reaction.

Authors:  Ruzhang Liu; Osvaldo Gutierrez; Dean J Tantillo; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2012-04-10       Impact factor: 15.419

5.  A Diastereoselective Intramolecular Pauson-Khand Approach to the Construction of the BC Ring System in Tuberostemoninol.

Authors:  Xiangna Jia; Robert M Williams
Journal:  Tetrahedron Asymmetry       Date:  2008-12-12

6.  Explorations of stemona alkaloid-inspired analogues: skeletal modification and functional group diversification.

Authors:  Kevin J Frankowski; Benjamin Neuenswander; Jeffrey Aubé
Journal:  J Comb Chem       Date:  2008-08-13

7.  One-pot synthesis of lactams using domino reactions: combination of Schmidt reaction with Sakurai and aldol reactions.

Authors:  Chan Woo Huh; Gagandeep K Somal; Christopher E Katz; Huaxing Pei; Yibin Zeng; Justin T Douglas; Jeffrey Aubé
Journal:  J Org Chem       Date:  2009-10-16       Impact factor: 4.354

8.  Synthesis of medium-bridged twisted lactams via cation-pi control of the regiochemistry of the intramolecular Schmidt reaction.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

9.  Diels-Alder exo selectivity in terminal-substituted dienes and dienophiles: experimental discoveries and computational explanations.

Authors:  Yu-hong Lam; Paul Ha-Yeon Cheong; José M Blasco Mata; Steven J Stanway; Véronique Gouverneur; K N Houk
Journal:  J Am Chem Soc       Date:  2009-02-11       Impact factor: 15.419

10.  Syntheses of the Stemona alkaloids (+/-)-stenine, (+/-)-neostenine, and (+/-)-13-epineostenine using a stereodivergent Diels-Alder/azido-Schmidt reaction.

Authors:  Kevin J Frankowski; Jennifer E Golden; Yibin Zeng; Yao Lei; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2008-04-09       Impact factor: 15.419
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