A modular synthesis of the lamellarin family of natural products has been developed that is based on the application of three iterative halogenation/cross-coupling reaction sequences. The ability to halogenate the pyrrole core in a regioselective fashion, even in the presence of highly electron-rich aryl substituents, has been established. The compatibility of Suzuki coupling conditions with free alcohols and phenols in the boronic acids has been employed to reduce the number of protection/deprotection steps. Indeed, the presence of a free phenol on boronic acid 3 has been determined to be critical for the successful final coupling in route to lamellarin G trimethyl ether, since protected versions fail to undergo coupling.
A Modular Synthesis of the Lamellarins: Total Synthesis of Lamellarin G Trimethyl Ether
Handy, ST., Zhang, Y., & Bregman, H. (2004). A Modular Synthesis of the Lamellarins: Total Synthesis of Lamellarin G Trimethyl Ether. Journal of Organic Chemistry, 69(7), 2362-2366. https://doi.org/10.1021/jo0352833
Abstract
Publications Info
To contact an RTI author, request a report, or for additional information about publications by our experts, send us your request.
Meet the Experts
View All ExpertsRecent Publications
Article
The daily association between affect and alcohol use: A meta-analysis of individual participant data
Article
Protection of forest ecosystems in the eastern United States from elevated atmospheric deposition of sulfur and nitrogen
Article
The use of patient experience feedback in rehabilitation quality improvement and codesign activities
Article