Total Synthesis of Yuzurine-type Alkaloid Daphgraciline.
J Am Chem Soc
; 144(41): 18823-18828, 2022 10 19.
Article
em En
| MEDLINE
| ID: mdl-36198113
ABSTRACT
The first total synthesis of daphgraciline has been achieved, which also represents the first example of the synthesis of Daphniphyllum yuzurine-type alkaloids (â¼50 members). The unique bridged azabicyclo[4.3.1] ring system in the yuzurine-type subfamily was efficiently and diastereoselectively assembled via a mild type II [5+2] cycloaddition for the first time. The compact tetracyclic [6-7-5-5] skeleton was installed efficiently via an intramolecular Diels-Alder reaction, followed by a benzilic acid-type rearrangement. The synthetically challenging spiro tetrahydropyran moiety in the final product was installed diastereoselectively via a TiIII-mediated reductive epoxide coupling reaction. Potential access to enantioenriched daphgraciline is presented.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Alcaloides
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article