Rapid biomimetic total synthesis of (±)-rossinone B.
A biomimetic total synthesis of (±)-rossinone B has been achieved through a highly efficient strategy featuring a series of rationally designed reactions, including a one-pot allylic rearrangement/oxidation reaction to generate the vinyl quinone 27, an intramolecular vinyl quinone Diels-Alder reaction to construct the linear 6-6-5 tricyclic core of 28, and a double conjugate addition/β-elimination cascade to complete the total synthesis of 1.
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry, Peking University, Beijing 100871, China.
Ziyang
Z
Zhang
Jiahua
J
Chen
Zhen
Z
Yang
Yefeng
Y
Tang
D001688:Biological Products / Q000737:chemistry; D040761:Biomimetic Materials / Q000138:chemical synthesis*; D015394:Molecular Structure; D013729:Terpenes / Q000138:chemical synthesis*
D001688:Biological Products; D013729:Terpenes; C547433:rossinone B