Yu X,
Xiao L,
Wang Z,
Luo T.
* Peking University, P. R. of China
Scalable Total Synthesis of (–)-Vinigrol.
J. Am. Chem. Soc. 2019;
141: 3440-3443
Key words
(–)-vinigrol - Cope rearrangement - Zweifel olefination - Diels–Alder reaction
Significance
The authors report the total synthesis of (–)-vinigrol, which has been an attractive target since its isolation in 1987. Key features of the synthesis include a transannular Diels–Alder reaction and an anionic Cope rearrangement.
Comment
The synthesis starts from (–)-limonene and gives ketone B following a known procedure. Anionic Cope rearrangement and further elaboration yield macrocycle H. Intramolecular Diels–Alder reaction gives access to the skeleton of vinigrol, which itself is obtained after five more steps.
