The Total Synthesis of Proteasome Inhibitors TMC-95A and TMC-95B: Discovery of a New Method To Generate cis-Propenyl Amides

The Total Synthesis of Proteasome Inhibitors TMC-95A and TMC-95B: Discovery of a New Method To Generate cis-Propenyl Amides

Silatropic and ene‐like bond reorganizations (see scheme, left) were the key steps in the first total synthesis of the title compounds, which only differ in stereochemistry at the remote C36 stereocenter. Other key steps include a Suzuki biaryl construction, a diastereofacial dihydroxylation reactio...

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Veröffentlicht in:Angewandte Chemie International Edition 2002-02, Vol.41 (3), p.512-515
Hauptverfasser: Lin, Songnian, Danishefsky, Samuel J.
Format: Artikel
Sprache:eng
Schlagworte:
Amides - chemistry
biaryls
Cysteine Endopeptidases
inhibitors
macrolactamization
Molecular Structure
Multienzyme Complexes - antagonists & inhibitors
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - chemistry
Peptides, Cyclic - pharmacology
Proteasome Endopeptidase Complex
rearrangement
Stereoisomerism
total synthesis
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Zusammenfassung:Silatropic and ene‐like bond reorganizations (see scheme, left) were the key steps in the first total synthesis of the title compounds, which only differ in stereochemistry at the remote C36 stereocenter. Other key steps include a Suzuki biaryl construction, a diastereofacial dihydroxylation reaction, and a macrolactamization.
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20020201)41:3<512::AID-ANIE512>3.0.CO;2-R