Beilstein J. Org. Chem.2023,19, 204–211, doi:10.3762/bjoc.19.19
The total synthesis of racemic incarvilleatone has been achieved by utilizing unexplored accelerated Rauhut–Currier (RC) dimerization. The other key steps of the synthesis are oxa-Michael and aldol reactions in a tandem sequence. Racemic incarvilleatone was separated by chiral HPLC and the
nonetheless, they exhibited very limited growth suppression activity.
Keywords: dimerization; incarviditone; incarvilleatone; oxa-Michael; Rauhut–Currier; Introduction
(±)-Incarvilleatone (1) is a dimeric cyclohexylethanoid isolated by Zhang and co-workers [1] in racemic form from the Chinese plant
Incarvillea younghusbandii (Figure 1). This plant is used in Chinese folk medicine to treat dizziness and anemia [1].
Zhang and co-workers [1] separated the racemic incarvilleatone in two individual enantiomers, (−)-incarvilleatone [(−)-1] and (+)-incarvilleatone [(+)-1] by performing chiral HPLC. The
PDF
Graphical Abstract
Figure 1:
Structures of (±)-incarvilleatone (1), (±)-incarviditone (2), and (±)-rengyolone (3).