The total synthesis of (±)-merrilactone A Journal Article
| Authors: | Birman, V. B.; Danishefsky, S. J. |
| Article Title: | The total synthesis of (±)-merrilactone A |
| Abstract: | The total synthesis of the title compound has been accomplished in 20 steps. The key step is a free radical cyclization of vinyl bromide 29 to afford 30. The synthesis also features an efficient Diels-Alder reaction of 2,3-dimethylmaleic anhydride with 1-(tert-butyldimethylsiloxy)-butadiene. The oxetane moiety of merrilactone A is fashioned via a Payne-like rearrangement of a hydroxyepoxide (see 2 → 1). Copyright © 2002 American Chemical Society. |
| Keywords: | unclassified drug; drug structure; drug synthesis; chemistry; cyclization; natural product; spectroscopy; oxidation; reaction analysis; synthesis; stereoisomerism; sesquiterpenes; lactone derivative; lactones; sesquiterpene; neurotrophic factor; lactone; isomerism; illicium; merrilactone a; article; illicium merrillianum extract |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 124 |
| Issue: | 10 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 2002-03-13 |
| Start Page: | 2080 |
| End Page: | 2081 |
| Language: | English |
| DOI: | 10.1021/ja012495d |
| PUBMED: | 11878938 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Export Date: 14 November 2014 -- Source: Scopus |
