Literature DB >> 19708701

Direct synthesis of medium-bridged twisted amides via a transannular cyclization strategy.

Michal Szostak1, Jeffrey Aubé.   

Abstract

The sequential RCM to construct a challenging medium-sized ring followed by a transannular cyclization across a medium-sized ring delivers previously unattainable twisted amides from simple acyclic precursors.

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Year:  2009        PMID： 19708701      PMCID： PMC2735017          DOI： 10.1021/ol901449y

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


  25 in total

1.  Synthesis of Medium-Sized Rings by the Ring-Closing Metathesis Reaction.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-06-16       Impact factor: 15.336

2.  Intramolecular Staudinger ligation: a powerful ring-closure method to form medium-sized lactams.

Authors:  Olivier David; Wim J N Meester; Hans Bieräugel; Hans E Schoemaker; Henk Hiemstra; Jan H van Maarseveen
Journal:  Angew Chem Int Ed Engl       Date:  2003-09-22       Impact factor: 15.336

3.  Asymmetric total synthesis of the 1-epi-aglycon of the cripowellins A and B.

Authors:  Dieter Enders; Achim Lenzen; Michael Backes; Carsten Janeck; Kelly Catlin; Marie-Isabelle Lannou; Jan Runsink; Gerhard Raabe
Journal:  J Org Chem       Date:  2005-12-09       Impact factor: 4.354

4.  Facile C-N cleavage in a series of bridged lactams.

Authors:  Yao Lei; Aaron D Wrobleski; Jennifer E Golden; Douglas R Powell; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

5.  Water-promoted hydrolysis of a highly twisted amide: rate acceleration caused by the twist of the amide bond.

Authors:  Jon Iñaki Mujika; Jose Maria Mercero; Xabier Lopez
Journal:  J Am Chem Soc       Date:  2005-03-30       Impact factor: 15.419

6.  Synthesis and structural analysis of 2-quinuclidonium tetrafluoroborate.

Authors:  Kousuke Tani; Brian M Stoltz
Journal:  Nature       Date:  2006-06-08       Impact factor: 49.962

7.  Indenylidene complexes of ruthenium: optimized synthesis, structure elucidation, and performance as catalysts for olefin metathesis--application to the synthesis of the ADE-ring system of nakadomarin A.

Authors:  A Fürstner; O Guth; A Düffels; G Seidel; M Liebl; B Gabor; R Mynott
Journal:  Chemistry       Date:  2001-11-19       Impact factor: 5.236

8.  Catalytic, asymmetric transannular aldolizations: total synthesis of (+)-hirsutene.

Authors:  Carley L Chandler; Benjamin List
Journal:  J Am Chem Soc       Date:  2008-05-03       Impact factor: 15.419

9.  The synthesis of pyrano- and furanopyrimidines from 3-haloprophyl- and 2-haloprophylbarbituric acids.

Authors:  E E Smissman; R A Robinson; A J Matuszak
Journal:  J Org Chem       Date:  1970-11       Impact factor: 4.354

10.  The synthesis of bicyclo(4,3.0) nonanebarbituric and -thiobarbituric acid derivatives and a bicyclo (4,4.0) decanebarbituric acid derivative.

Authors:  E E Smissman; J W Ayres
Journal:  J Org Chem       Date:  1971-08-27       Impact factor: 4.354
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  7 in total

1.  Structural characterization of N-protonated amides: regioselective N-activation of medium-bridged twisted lactams.

Authors:  Michal Szostak; Lei Yao; Victor W Day; Douglas R Powell; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

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.  A modular reaction pairing approach to the diversity-oriented synthesis of fused- and bridged-polycyclic sultams.

Authors:  Thiwanka B Samarakoon; Joanna K Loh; Alan Rolfe; Lisa S Le; Sun Young Yoon; Gerald H Lushington; Paul R Hanson
Journal:  Org Lett       Date:  2011-09-07       Impact factor: 6.005

4.  Novel tetracyclic structures from the synthesis of thiolactone-isatin hybrids.

Authors:  Renate Hazel Hans; Hong Su; Kelly Chibale
Journal:  Beilstein J Org Chem       Date:  2010-07-19       Impact factor: 2.883

5.  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

6.  Proximity effects in nucleophilic addition reactions to medium-bridged twisted lactams: remarkably stable tetrahedral intermediates.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419

7.  Uncovering the importance of proton donors in TmI2-promoted electron transfer: facile C-N bond cleavage in unactivated amides.

Authors:  Michal Szostak; Malcolm Spain; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-12       Impact factor: 15.336
  7 in total

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