Strategies, setbacks, and successes in the synthesis of (−)-spiroleucettadine
- Author(s)
- Lamb, Richard A; Lucas, Nigel T; Lessene, Guillaume; Hawkins, Bill C;
- Details
- Publication Year 2018-09-07,Volume 83,Issue #17,Page 10120-10133
- Journal Title
- Journal of Organic Chemistry
- Publication Type
- Journal Article
- Abstract
- Various strategies toward the synthesis of the marine natural product (−)-spiroleucettadine are described. In the original strategy, a biomimetic inspired oxidation of a 2-imidazoline scaffold uncovered unexpected reactivity, where benzylic oxidation followed by a Baeyer–Villiger reaction was observed. The second generation approach examined oxidative dearomatization of the phenol ring system first, where a competing spirocyclization process was uncovered. Efforts to forge the scaffold via a carbocation mediated benzyl migration were unsuccessful. Highlights of the successful synthesis include two consecutive hypervalent iodine reactions: the first formed the spirocyclic center and the second facilitated installation of an acetate group at the C-5 position to allow for subsequent introduction of the methyl amine side chain.
- Publisher
- American Chemical Society
- Research Division(s)
- Chemical Biology
- Publisher's Version
- https://doi.org/10.1021/acs.joc.8b01404
- Terms of Use/Rights Notice
- Refer to copyright notice on published article.
Creation Date: 2019-02-05 08:28:48
Last Modified: 2019-02-05 08:45:23