Biomimetic total synthesis of (+)-chabranol.
A concise, biomimetic total synthesis of the unprecedented terpenoid skeleton (+)-chabraol has been accomplished via 6 steps from the chiral epoxide 7, involving an intramolecular Prins double cyclization to yield the bicyclo[2.2.1] core of the natural product as the key step. The absolute configuration of natural chabranol was also designated through the first asymmetric total synthesis.
Wang
Xiaolei
X
State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
Zheng
Jie
J
Chen
Qiang
Q
Zheng
Huaiji
H
He
Yongping
Y
Yang
Juan
J
She
Xuegong
X
D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D018716:Molecular Mimicry; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D013729:Terpenes; C545600:chabranol