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Total Synthesis of Farnesin through an Excited‐State Nazarov Reaction
Author(s) -
Que Yonglei,
Shao Hao,
He Haibing,
Gao Shuanhu
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202001350
Subject(s) - excited state , state (computer science) , chemistry , photochemistry , computer science , physics , atomic physics , algorithm
The asymmetric total synthesis of farnesin, a rearranged ent ‐kaurenoid, was achieved through a convergent approach involving photo‐Nazarov and intramolecular aldol cyclizations to build the syn‐syn‐syn hydrofluorenol ABC ring system and bicyclo[3.2.1]octane CD ring system in the first application of a UV‐light‐induced excited‐state Nazarov cyclization of a non‐aromatic dicyclic divinyl ketone in a total synthesis. Unlike the conventional acid‐promoted ground‐state Nazarov reaction, the excited‐state Nazarov reaction enables stereospecific formation of the highly strained syn‐syn‐syn ‐fused hydrofluorenone scaffold through a disrotatory cyclization.