Total synthesis of (-)-orthodiffenes A and C.
The efficient and concise synthesis of (-)-orthodiffenes A and C has been accomplished for the first time in eight steps from readily available chiral synthons, D-mannose and D-ethyl lactate. Our work confirmed the complete structure of orthodiffenes A and C, including their absolute stereochemistry. The key steps of our total synthesis involved cis-fused tetrahydrofuran cyclization, one-pot deprotection-lactonization, and intramolecular benzoyl migration according to a biosynthetic hypothesis of orthodiffenes.
State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China. junliu@rcees.ac.cn
Jun
J
Liu
Yi
Y
Liu
Xing
X
Zhang
Chaoli
C
Zhang
Yangguang
Y
Gao
LinLin
L
Wang
Yuguo
Y
Du
D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D007773:Lactates / Q000138:chemical synthesis* / Q000737:chemistry*; D008358:Mannose / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D005663:Furans; D007773:Lactates; C578826:orthodiffene A; C578825:orthodiffene B; C578824:orthodiffene C; C015866:ethyl lactate; D008358:Mannose