Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 3, Pages 339-347Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201901613
Keywords
Butenolides; Oxygen heterocycles; Radical reactions; Singlet oxygen; Synthetic methods
Categories
Funding
- Shanghai Rising-Star Plan [17QA1405100]
- Thousand Youth Talents Plan
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- CAS Key Laboratory of Synthetic Chemistry of Natural Substances
- Shanghai Institute of Organic Chemistry
Ask authors/readers for more resources
The development of new chemical transformations to simplify the synthesis of valuable building blocks is a challenging task in organic chemistry and has been the focus of considerable research effort. Here we report a chemical transformation that enables the facile and modular synthesis of synthetically challenging yet biologically important functionalized butenolides from easily accessible furans. Specifically, Diels-Alder reactions between furans and singlet oxygen generate versatile hydroperoxide intermediates, which undergo iron(II)-mediated radical fragmentation in the presence of Cu(OAc)(2) or various radical trapping reagents to afford butenolides bearing a wide variety of appended remote functional groups, including olefins, halides, azides, and aldehydes. The practical utility of this transformation is demonstrated by easy diversification of the products by means of cross-coupling reactions and, most importantly, by its ability to simplify the syntheses of known building blocks of eight biologically active natural products.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available