Enantioselective and collective syntheses of xanthanolides involving a controllable dyotropic rearrangement of cis-β-lactones.
Let's swap: a scalable, atom-economic, enantio-, and diastereoselective synthetic route to trisubstituted γ-butyrolactones based on a Wagner-Meerwein-type dyotropic rearrangement of cis-β-lactones is described. This methodology was applied in efficient and protecting-group-free formal syntheses and total syntheses of various xanthanolide natural products.
The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing, China.
Weiwu
W
Ren
Yichao
Y
Bian
Ziyang
Z
Zhang
Hai
H
Shang
Pengtao
P
Zhang
Yuejie
Y
Chen
Zhen
Z
Yang
Tuoping
T
Luo
Yefeng
Y
Tang
D015107:4-Butyrolactone / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism; D031210:Xanthium / Q000737:chemistry*
D001688:Biological Products; D007783:Lactones; D012717:Sesquiterpenes; D015107:4-Butyrolactone