Literature DB >> 11348175

Total synthesis of the immunosuppressant FR901483 via an amidoacrolein cycloaddition.

J H Maeng1, R L Funk.   

Abstract

[reaction: see text]. The total synthesis of the potent immunosuppressant FR901483 is described. In a key step, the intermolecular Diels-Alder cycloaddition of an amidoacrolein with 2-(triisopropylsilyloxy)-1,3-butadiene produced the desired 3-cyclohexene-1-carboxaldehyde. This compound was subjected to basic followed by acidic conditions which effected two sequential aldol cyclizations to deliver the tricyclic ring system of the natural product, suitably functionalized for completion of the total synthesis.

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Year:  2001        PMID： 11348175     DOI： 10.1021/ol015506g

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


  9 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.  Studies on total synthesis of the cylindricine/fasicularin/lepadiformine family of tricyclic marine alkaloids.

Authors:  Steven M Weinreb
Journal:  Chem Rev       Date:  2006-06       Impact factor: 60.622

3.  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

4.  Enantioselective Synthesis of the Tricyclic Core of FR901483 Featuring a Rh-Catalyzed [2+2+2] Cycloaddition.

Authors:  Stéphane Perreault; Tomislav Rovis
Journal:  Synthesis (Stuttg)       Date:  2013       Impact factor: 3.157

5.  Enantioselective synthesis of indolizidines bearing quaternary substituted stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes.

Authors:  Ernest E Lee; Tomislav Rovis
Journal:  Org Lett       Date:  2008-02-20       Impact factor: 6.005

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.  Total synthesis of indolizidine alkaloid (-)-209D: overriding substrate bias in the asymmetric rhodium-catalyzed [2+2+2] cycloaddition.

Authors:  Robert T Yu; Ernest E Lee; Guillaume Malik; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  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

9.  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
  9 in total

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