Racemic total synthesis of dactyloidin and demethyldactyloidin through the DL-proline-catalyzed Knoevenagel condensation/[4 + 2] cycloaddition cascade.
An efficient approach towards the first racemic total synthesis of dactyloidin (2) and demethyldactyloidin (3) is described. Their oxygen-bridged tricyclic ketal systems were rapidly constructed by using a remarkable biomimetic Knoevenagel condensation/[4 + 2] cycloaddition cascade as the critical strategy and the 1,5-dicarbonyl segment was assembled by Grignard addition.
Program for Natural Product Chemical Biology, Key Laboratory Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, People's Republic of China. sxqiu@scbg.ac.cn tanhaibo@scbg.ac.cn.
Haibo
H
Tan
Hongxin
H
Liu
Xinzheng
X
Chen
Huiyu
H
Chen
Shengxiang
S
Qiu
D002384:Catalysis; D061565:Cycloaddition Reaction / Q000379:methods*; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D008745:Methylation; D026324:Myristicaceae / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
D006572:Heterocyclic Compounds, Bridged-Ring; C000609244:dactyloidin; D011392:Proline