Total Synthesis of (+)-Hyacinthacine A1 Using a Chemoselective Cross-Benzoin Reaction and a Furan Photooxygenation-Amine Cyclization Strategy.
Org Lett
; 23(4): 1416-1421, 2021 02 19.
Article
em En
| MEDLINE
| ID: mdl-33538602
ABSTRACT
We report the shortest synthesis of glycosidase inhibitor (+)-hyacinthacine A1 using a highly chemoselective N-heterocyclic carbene-catalyzed cross-benzoin reaction as well as a furan photooxygenation-amine cyclization strategy. This is the first such cyclization on a furylic alcohol, an unprecedented reaction due to the notorious instability of the formed intermediates. The photooxygenation strategy was eventually incorporated into a three-step one-pot process that formed the requisite pyrrolizidine framework of (+)-hyacinthacine A1.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Benzoína
/
Furanos
/
Aminas
/
Metano
Idioma:
En
Ano de publicação:
2021
Tipo de documento:
Article