posted on 2023-04-07, 14:34authored byXiangyu Zhuang, Chenghong Sun, Pengzhen Fu, Changhai Yu, Jie Jiang, Shuangshuang Wang, Xuefeng Xiao, Bin Wang
Loganetin is the aglycone moiety
of loganin that has
a 5,6-fused
bicyclic framework and exhibits a wide range of interesting biological
activities. A gram-scale synthesis of loganetin has been accomplished
from the readily accessible S-(+)-carvone. The key
reactions of the synthesis are a Favorskii rearrangement to introduce
four stereocenters and a sulfuric acid-meditated deprotection/cyclization
reaction to assemble the sensitive dihydropyran ring with complete
stereoselectivity. This work also enables us to synthesize C1 methoxy
loganetin and the enantiomer of loganetin successfully.