Enantioselective Total Synthesis of (+)-Sieboldine A and Analogues Thereof.
Org Lett
; 24(41): 7517-7521, 2022 Oct 21.
Article
in En
| MEDLINE
| ID: mdl-36214606
ABSTRACT
An 11-step enantioselective total synthesis of (+)-sieboldine A (1) has been accomplished from (5R)-methylcyclohex-2-en-1-one (16), in which an intramolecular ketone/ester reductive coupling followed by one-pot acidic treatment to quickly construct the unique oxa-spiroacetal and a TsOH-catalyzed displacement to directly form the characteristic N-hydroxyazacyclononane ring successfully served as the key methodologies. Moreover, several full-skeleton analogues of 1 were also synthesized on the basis of the advanced intermediates, and their inhibitory effects on electric eel acetylcholinesterase were examined.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Acetylcholinesterase
/
Ketones
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2022
Document type:
Article
Affiliation country:
China