The Structural Revision and Total Synthesis of Carambolaflavone A

The synthesis of both enantiomers of carambolaflavone A, the antidiabetic and flavonoid C-glycoside, was achieved for the first time via a 12-longest-linear-step with 16% (l-fucose) and 11% (d-fucose) overall yields. Through the synthetic investigation, the adverse effect of 4A MS in Suzuki C-glycos...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2018-04, Vol.83 (7), p.4111-4118
Main Authors: Wang, Yong, Liu, Miao, Liu, Lei, Xia, Jian-Hui, Du, Yu-Guo, Sun, Jian-Song
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The synthesis of both enantiomers of carambolaflavone A, the antidiabetic and flavonoid C-glycoside, was achieved for the first time via a 12-longest-linear-step with 16% (l-fucose) and 11% (d-fucose) overall yields. Through the synthetic investigation, the adverse effect of 4A MS in Suzuki C-glycosylation was disclosed, the mechanism of hydrogen-bonded-phenol involved Suzuki C-glycosylation was clarified, and the authentic structure of carambolaflavone A was also determined.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b00008