Literature DB >> 22199407

Synthesis of the C21-C34 fragment of antascomicin B.

John M Hutchison1, Andrew S Gibson, David T Williams, Matthias C McIntosh.   

Abstract

The C21-C34 fragment of the potent FKBP12-binding macrolide antascomicin B was prepared using Ireland-Claisen and allylic diazene rearrangements to establish the C26/C27 and the C23 stereocenters, respectively. Directed hydrogenation installed the C29 β-configuration. The fragment possesses 7 of the 11 fixed stereocenters contained in the natural product.

Entities:  

Year:  2011        PMID： 22199407      PMCID： PMC3244276          DOI： 10.1016/j.tetlet.2011.09.027

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  20 in total

1.  Total synthesis of antascomicin B.

Authors:  Dominic E A Brittain; Charlotte M Griffiths-Jones; Michael R Linder; Martin D Smith; Catherine McCusker; Jaqueline S Barlow; Ryo Akiyama; Kosuke Yasuda; Steven V Ley
Journal:  Angew Chem Int Ed Engl       Date:  2005-04-29       Impact factor: 15.336

2.  Efficient diastereoselective synthesis of trifarane-type sesquiterpenes, trifarienols A and B.

Authors:  Kazunori Takahashi; Ryuichi Akao; Toshio Honda
Journal:  J Org Chem       Date:  2009-05-01       Impact factor: 4.354

3.  Antascomicins A, B, C, D and E. Novel FKBP12 binding compounds from a Micromonospora strain.

Authors:  T Fehr; J J Sanglier; W Schuler; L Gschwind; M Ponelle; W Schilling; C Wioland
Journal:  J Antibiot (Tokyo)       Date:  1996-03       Impact factor: 2.649

4.  Efficient, scalable asymmetric synthesis of an epoxy quinol via Noyori desymmetrization of a meso diketone.

Authors:  David R Clay; Ashley G Rosenberg; Matthias C McIntosh
Journal:  Tetrahedron Asymmetry       Date:  2011-04-10

5.  Synthesis and stereochemical confirmation of the secoiridoid glucosides nudiflosides D and A.

Authors:  Stephen Hanessian; Emily Mainetti; Fabien Lecomte
Journal:  Org Lett       Date:  2006-08-31       Impact factor: 6.005

Review 6.  Immunophilins: for the love of proteins.

Authors:  S Barik
Journal:  Cell Mol Life Sci       Date:  2006-12       Impact factor: 9.261

7.  Synthesis, molecular modeling and biological evaluation of aza-proline and aza-pipecolic derivatives as FKBP12 ligands and their in vivo neuroprotective effects.

Authors:  Douglas E Wilkinson; Bert E Thomas; David C Limburg; Agnes Holmes; Hansjorg Sauer; Douglas T Ross; Raj Soni; Yi Chen; Hong Guo; Pamela Howorth; Heather Valentine; Dawn Spicer; Mike Fuller; Joseph P Steiner; Gregory S Hamilton; Yong-Qian Wu
Journal:  Bioorg Med Chem       Date:  2003-11-03       Impact factor: 3.641

8.  Catalytic asymmetric synthesis of palmerolide A via organoboron methodology.

Authors:  Marlin Penner; Vivek Rauniyar; Ludwig T Kaspar; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

9.  Toward the Synthesis of Antascomicin B. Synthesis of a Model of the C22-C34 Fragment via Ireland-Claisen and Allylic Diazene Rearrangements.

Authors:  Wei Qi; Matthias C McIntosh
Journal:  Tetrahedron       Date:  2008       Impact factor: 2.457

Review 10.  Total synthesis studies on macrocyclic pipecolic acid natural products: FK506, the antascomicins and rapamycin.

Authors:  Matthew L Maddess; Miles N Tackett; Steven V Ley
Journal:  Prog Drug Res       Date:  2008
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  1 in total

1.  Anomalies in the asymmetric transfer hydrogenation of several polycyclic meso compounds.

Authors:  David R Clay; Matthias C McIntosh
Journal:  Tetrahedron Lett       Date:  2012-01-14       Impact factor: 2.415
  1 in total

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