Total Syntheses of (+)-Villocarine A, (-)-Apogeissoschizine, and (+)-Geissoschizine.
Chemistry
; 29(18): e202300179, 2023 Mar 28.
Article
in En
| MEDLINE
| ID: mdl-36670343
ABSTRACT
Total syntheses of geissoschizine-type monoterpenoid indole alkaloids (MTIAs) are reported. An intramolecular Pictet-Spengler cyclization was developed for the selective construction of the 3R stereocenter. The first total synthesis of (+)-villocarineâ
A was then achieved. Furthermore, the first total synthesis of the highly strained (-)-apogeissoschizine was also accomplished in an aza-Michael cyclization/E1cB elimination/stereoselective olefin isomerization sequence. Finally, (+)-geissoschizine, a common biosynthetic intermediate of MTIAs, was obtained from apogeissoschizine through ring-opening along with a release of ring strain.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Chemistry
Journal subject:
QUIMICA
Year:
2023
Document type:
Article
Affiliation country:
Japan