Concise Construction of the Tricyclic Core of Bullataketals Enabled by a Biomimetic Intermolecular (3 + 3) Type Cycloaddition.
A remarkable TFA-mediated method for the construction of a biologically interesting tricyclic ketal skeleton was uncovered by starting from a variety of readily available acylphloroglucinol and diacylphloroglucinol substrates. This approach, which mimics a biosynthetic olefin isomerization/hemiacetalization/dehydration/(3 + 3) type cycloaddition sequence through a 2H-furan-1-ium intermediate, establishes a viable synthetic strategy for efficient synthesis of bullataketals' analogs.
†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.
Haibo
H
Tan
†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.
Hongxin
H
Liu
‡School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen 518055, People's Republic of China.
Xinzheng
X
Chen
†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.
Yunfei
Y
Yuan
§School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, People's Republic of China.
Kai
K
Chen
†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.
Shengxiang
S
Qiu
D000475:Alkenes / Q000737:chemistry; D032701:Biomimetics; D003500:Cyclization; D061565:Cycloaddition Reaction; D004987:Ethers; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D004987:Ethers; D007659:Ketones; C506715:bullataketal A; D010696:Phloroglucinol