In:
Angewandte Chemie International Edition, Wiley, Vol. 59, No. 19 ( 2020-05-04), p. 7444-7449
Kurzfassung:
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.
Materialart:
Online-Ressource
ISSN:
1433-7851
,
1521-3773
DOI:
10.1002/anie.202001350
Sprache:
Englisch
Verlag:
Wiley
Publikationsdatum:
2020
ZDB Id:
2011836-3
ZDB Id:
123227-7