Literature DB >> 11348231

Tandem cationic aza-cope rearrangement-Mannich cyclization approach to the core structure of FR901483 via a Bridgehead iminium ion.

K M Brummond1, J Lu.   

Abstract

[reaction in text] An approach to the potent immunosuppressant FR901483 is described. This route utilizes a tandem cationic aza-Cope rearrangement-Mannich cyclization to generate the core structure of this compound. In addition, this is the first demonstration of this tandem reaction passing through a bridgehead iminium ion.

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Year:  2001        PMID: 11348231     DOI: 10.1021/ol010029n

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


  8 in total

1.  A Synthesis of the Tricyclic Core Structure of FR901483 Featuring an Ugi Four-Component Coupling and a Remarkably Selective Elimination Reaction.

Authors:  Hirofumi Seike; Erik J Sorensen
Journal:  Synlett       Date:  2008-03-18       Impact factor: 2.454

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

Review 3.  Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Authors:  Amanda C Jones; Jeremy A May; Richmond Sarpong; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-03       Impact factor: 15.336

4.  Synthetic studies toward (-)-FR901483 using a conjugate allylation to install the C-1 quaternary carbon.

Authors:  Dimitar B Gotchev; Daniel L Comins
Journal:  J Org Chem       Date:  2006-12-08       Impact factor: 4.354

5.  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

6.  Studies on a total synthesis of the microbial immunosuppresive agent FR901483.

Authors:  Jeffrey E Kropf; Ivona C Meigh; Magnus W P Bebbington; Steven M Weinreb
Journal:  J Org Chem       Date:  2006-03-03       Impact factor: 4.354

7.  Toward the total synthesis of FR901483: concise synthesis of the azatricyclic skeleton.

Authors:  Suvi T M Simila; Stephen F Martin
Journal:  J Org Chem       Date:  2007-06-08       Impact factor: 4.354

8.  Biosynthesis of the Immunosuppressant (-)-FR901483.

Authors:  Zhuan Zhang; Yui Tamura; Mancheng Tang; Tianzhang Qiao; Michio Sato; Yoshihiro Otsu; Satoshi Sasamura; Masatoshi Taniguchi; Kenji Watanabe; Yi Tang
Journal:  J Am Chem Soc       Date:  2020-12-29       Impact factor: 15.419

  8 in total

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