Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 20, Pages 8120-8123Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo8016956
Keywords
-
Categories
Funding
- National Science Foundation [CHE-0742663]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0742663] Funding Source: National Science Foundation
Ask authors/readers for more resources
The intramolecular Diels-Alder reaction of several amidofurans tethered onto a benzofuran ring was examined as a strategy for the synthesis of morphine. Bromo substitution on the furan ring did not provide sufficient activation to allow the cycloaddition to take place across the aromatic benzofuran. However, the presence of a large o-methylbenzyl group on the amido nitrogen atom causes the reactive s-trans conformation of the amidofuran to be highly populated, thereby facilitating its Diels-Alder cycloaddition across a tethered benzofuran.
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