The total synthesis of frondosin B Journal Article
| Authors: | Inoue, M.; Frontier, A. J.; Danishefsky, S. J. |
| Article Title: | The total synthesis of frondosin B |
| Abstract: | The interleukin-8 receptor antagonist frondosin B (1) was synthesized in 12 steps from commercially available 5-methoxysalicylaldehyde in a completely regiocontrolled manner. The key steps of the synthesis were a Friedel-Crafts reaction to form the 7-membered ring and a Diels-Alder reaction to build the 6-membered ring, thereby fixing the double bond in the proper position. |
| Keywords: | unclassified drug; nonhuman; drug structure; drug synthesis; nuclear magnetic resonance spectroscopy; thermodynamics; natural product; chemical reaction; drug isolation; total synthesis; stereochemistry; cycloadditions; natural products; bicyclo compound; receptor blocking agent; benzofuran derivative; sponge (porifera); optical rotation; article; frondosin b; interleukin 8 receptor; cyclizations; salicylaldehyde; sesquiterpenoid |
| Journal Title: | Angewandte Chemie - International Edition |
| Volume: | 39 |
| Issue: | 4 |
| ISSN: | 1433-7851 |
| Publisher: | Wiley Blackwell |
| Date Published: | 2000-02-01 |
| Start Page: | 761 |
| End Page: | 764 |
| Language: | English |
| DOI: | 10.1002/(sici)1521-3773(20000218)39:4<761::aid-anie761>3.0.co;2-i |
| PROVIDER: | scopus |
| PUBMED: | 10760861 |
| DOI/URL: | |
| Notes: | Export Date: 18 November 2015 -- Source: Scopus |
