Total synthesis of (-)-talaumidin and (-)-galbelgin.
( - )-Talaumidin (1) and ( - )-galbelgin (2) have been synthesized via 4-pentenoic acid as a starting material with the overall yield of about 17.8 and 16.9%, respectively. The key steps include Evans asymmetry anti-aldol reaction, TBS protection, hydroboration, oxidation, Friedel-Crafts arylation, etc.
Xue
Peng
P
Peking Union Medical College and Chinese Academy of Medical Sciences, Institute of Materia Medica, Beijing, China.
Wang
Li-Ping
LP
Jiao
Xiao-Zhen
XZ
Jiang
Ying-Jun
YJ
Xiao
Qiong
Q
Luo
Zhi-Gang
ZG
Xie
Ping
P
Liang
Xiao-Tian
XT
D000447:Aldehydes / Q000737:chemistry; D005229:Fatty Acids, Monounsaturated / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D005229:Fatty Acids, Monounsaturated; D005663:Furans; D017705:Lignans; C492479:talaumidin; C084077:galgravin; C116609:3-hydroxybutanal; C009785:4-pentenoic acid