Enantioselective total synthesis of (+)-Lingzhiol via tandem semipinacol rearrangement/Friedel-Crafts type cyclization.
Enantioselective total synthesis of (+)-Lingzhiol has been achieved. It is the first example of in tandem semipinacol rearrangement reactions, the migrated aryl group further reacting with the carbonyl oxonium electrophile to furnish a polycyclic skeleton. Our synthesis involves 13 steps and proceeds in 6% overall yield.
State Key Laboratory of Photochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, P. R. China. qinhongbo@mail.kib.ac.cn and University of Chinese Academy of Sciences, Beijing 100049, P. R. China.
Dong
D
Chen
State Key Laboratory of Photochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, P. R. China. qinhongbo@mail.kib.ac.cn and University of Chinese Academy of Sciences, Beijing 100049, P. R. China.
Wen-Dan
WD
Xu
State Key Laboratory of Photochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, P. R. China. qinhongbo@mail.kib.ac.cn and University of Chinese Academy of Sciences, Beijing 100049, P. R. China.
Hao-Miao
HM
Liu
Yunnan Baiyao Group Corporation Limited, Kunming 650032, China.
Ming-Ming
MM
Li
State Key Laboratory of Photochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, P. R. China. qinhongbo@mail.kib.ac.cn.
Yong-Min
YM
Yan
State Key Laboratory of Photochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, P. R. China. qinhongbo@mail.kib.ac.cn.
Xiao-Nian
XN
Li
State Key Laboratory of Photochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, P. R. China. qinhongbo@mail.kib.ac.cn.
Yan
Y
Li
State Key Laboratory of Photochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, P. R. China. qinhongbo@mail.kib.ac.cn.
Yong-Xian
YX
Cheng
State Key Laboratory of Photochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, P. R. China. qinhongbo@mail.kib.ac.cn.
Hong-Bo
HB
Qin