The total synthesis of (+)-migrastatin Journal Article
| Authors: | Gaul, C.; Njardarson, J. T.; Danishefsky, S. J. |
| Article Title: | The total synthesis of (+)-migrastatin |
| Abstract: | The first total synthesis of (+)-migrastatin, a macrolide natural product with interesting antimetastatic properties, has been accomplished. Our concise and flexible approach utilizes a Lewis acid-catalyzed diene aldehyde condensation to install the three contiguous stereocenters and the trisubstituted (Z)-alkene of migrastatin. Construction of the two remaining stereocenters and incorporation of the glutarimide-containing side chain have been achieved via an anti-selective aldol reaction, followed by a Horner-Wadsworth-Emmons olefination. Finally, the assembly of the macrocycle has been realized by a highly (E)-selective ring-closing metathesis. Copyright © 2003 American Chemical Society. |
| Keywords: | unclassified drug; methylation; antineoplastic agents; drug structure; drug synthesis; polymerization; natural product; structure analysis; drug isolation; ring closing metathesis; chelation; stereochemistry; stereoisomerism; lactones; acylation; migrastatin; streptomyces; macrolides; piperidones; article |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 125 |
| Issue: | 20 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 2003-05-21 |
| Start Page: | 6042 |
| End Page: | 6043 |
| Language: | English |
| DOI: | 10.1021/ja0349103 |
| PUBMED: | 12785819 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Export Date: 12 September 2014 -- Source: Scopus |
