The total synthesis of proteasome inhibitors TMC-95A and TMC-95B: Discovery of a new method to generate cis-propenyl amides Journal Article
| Authors: | Lin, S.; Danishefsky, S. J. |
| Article Title: | The total synthesis of proteasome inhibitors TMC-95A and TMC-95B: Discovery of a new method to generate cis-propenyl amides |
| Abstract: | 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. |
| Keywords: | unclassified drug; proteasome; proteasome inhibitor; proteasome endopeptidase complex; drug synthesis; structure activity relation; chemistry; drug antagonism; chemical structure; molecular structure; multienzyme complex; ic 50; multienzyme complexes; enzymes; synthesis; total synthesis; synthesis (chemical); peptides, cyclic; cyclopeptide; stereochemistry; stereoisomerism; cell membrane permeability; amides; amide; inhibitors; hydroxylation; fermentation; isomer; rearrangement; cysteine proteinase; cysteine endopeptidases; tmc-95a; article; tmc 95a; tmc 95b; support, u.s. gov't, p.h.s.; support, u.s. gov't, non-p.h.s.; biaryls; macrolactamization; dehydroxylation; tmc-95b |
| Journal Title: | Angewandte Chemie - International Edition |
| Volume: | 41 |
| Issue: | 3 |
| ISSN: | 1433-7851 |
| Publisher: | Wiley Blackwell |
| Date Published: | 2002-12-01 |
| Start Page: | 512 |
| End Page: | 515 |
| Language: | English |
| DOI: | 10.1002/1521-3773(20020201)41:3<512::aid-anie512>3.0.co;2-r |
| PUBMED: | 12491396 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Export Date: 14 November 2014 -- Source: Scopus |
