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Literature DB >> 15149232

Total synthesis of TMC-95A and -B via a new reaction leading to Z-enamides. Some preliminary findings as to SAR.

Songnian Lin¹, Zhi-Qiang Yang, Benjamin H B Kwok, Michael Koldobskiy, Craig M Crews, Samuel J Danishefsky.

Abstract

A full account of the total syntheses of proteasome inhibitors TMC-95A and -B is provided. A key feature of the syntheses involved installation of a cis-propenylamide moiety by a thermal rearrangement of an alpha-silylallyl amide. The scope and mechanism of the enamide-forming reaction are discussed. Also provided are some preliminary results from SAR studies. It was found that simplified analogues can retain the full potency of proteasome inhibition.

Entities: Chemical Gene

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Year: 2004 PMID： 15149232 PMCID： PMC2507741 DOI： 10.1021/ja049821k

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

19 in total

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4. Synthesis of the Functionalized Macrocyclic Core of Proteasome Inhibitors TMC-95A and B This work was supported by grants from the National Institutes of Health (grant CA28824). We thank Dr. George Sukenick and Sylvi Rusli of the MSKCC NMR Core Facility for NMR and mass spectral analyses (NIH Grant CA08748).

Authors: Songnian Lin; Samuel J. Danishefsky
Journal: Angew Chem Int Ed Engl Date: 2001-05-18 Impact factor: 15.336

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8. Stereocontrolled synthesis of the northern part of potent proteasome inhibitor TMC-95A.

Authors: M Inoue; H Furuyama; H Sakazaki; M Hirama
Journal: Org Lett Date: 2001-09-06 Impact factor: 6.005

9. Mechanism of cis-enamide formation from N-(alpha-silyl)allyl amides: synthetic potential of stepwise dyotropic rearrangements.

Authors: Xiyun Zhang; K N Houk; Songnian Lin; Samuel J Danishefsky
Journal: J Am Chem Soc Date: 2003-04-30 Impact factor: 15.419

10. Structures of TMC-95A-D: novel proteasome inhibitors from Apiospora montagnei sacc. TC 1093.

Authors: J Kohno; Y Koguchi; M Nishio; K Nakao; M Kuroda; R Shimizu; T Ohnuki; S Komatsubara
Journal: J Org Chem Date: 2000-02-25 Impact factor: 4.354

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2. Isomerization of N-Allyl Amides To Form Geometrically Defined Di-, Tri-, and Tetrasubstituted Enamides.

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Journal: J Am Chem Soc Date: 2017-04-04 Impact factor: 15.419

3. A concise formal synthesis of diazonamide A by the stereoselective construction of the C10 quaternary center.

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Authors: Buddy Soto-Cairoli; Jorge Justo de Pomar; John A Soderquist
Journal: Org Lett Date: 2007-12-20 Impact factor: 6.005

5. A One-Pot Divergent Sequence to Pyrazole and Quinoline Derivatives.

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6. Pharmacomodulation of the Antimalarial Plasmodione: Synthesis of Biaryl- and N-Arylalkylamine Analogues, Antimalarial Activities and Physicochemical Properties.

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