Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 65, Issue 23, Pages 8011-8019Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0010936
Keywords
-
Categories
Funding
- NIGMS NIH HHS [GM35727] Funding Source: Medline
Ask authors/readers for more resources
The total synthesis of the dimeric ellagitannin coriariin A is reported. The key reaction to access the dimeric framework was realized early in the synthesis pathway via a bis acylation reaction of a dehydrodigalloyl diacid with 2 equiv of a glucopyranose trichloroacetimidate. The glucose rings were subsequently functionalized, culminating in a double oxidative cyclization to form stereoselectively both (S)-HHDP ester units. This bis acylation strategy was also employed to prepare a gallotannin analogue of coriariin A whose earlier synthesis by orthoquinone dimerization was plagued by yield-limiting side reactions.
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