Literature DB >> 15281755

Stereocontrolled total synthesis of potent immunosuppressant FR901483.

Toshiyuki Kan1, Teppei Fujimoto, Shigeru Ieda, Yusuke Asoh, Haruka Kitaoka, Tohru Fukuyama.   

Abstract

A total synthesis of the potent immunosuppressant FR901483 (1) has been accomplished. The key feature of our convergent synthesis is the stereoselective incorporation of the p-methoxybenzyl and methylamino groups within the core moiety 10. Tricycle 10 was itself constructed by an intramolecular aldol reaction of the symmetrical keto-aldehyde 7. [Structure: see text]

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Year:  2004        PMID： 15281755     DOI： 10.1021/ol049074w

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

2.  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

3.  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

4.  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

5.  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

6.  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

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

9.  Enantioselective desymmetrization of prochiral cyclohexanones by organocatalytic intramolecular Michael additions to α,β-unsaturated esters.

Authors:  Adam D Gammack Yamagata; Swarup Datta; Kelvin E Jackson; Linus Stegbauer; Robert S Paton; Darren J Dixon
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-27       Impact factor: 15.336
  9 in total

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