Bioinspired Total Synthesis of 3-epi-Junipercedrol.
Org Lett
; 26(35): 7463-7467, 2024 Sep 06.
Article
en En
| MEDLINE
| ID: mdl-39190923
ABSTRACT
A bioinspired total synthesis of 3-epi-junipercedrol, which contains a strained tricyclo[5.2.2.03,7]undecane allo-cedrane framework and five stereocenters, was accomplished via an effective anionic semipinacol rearrangement of a tricyclic cedrane mesylate. The corresponding cedrane precursor was synthesized efficiently by employing the reductive oxy-Nazarov cyclization and an intramolecular aldol condensation as the key steps. This synthetic approach provided a further evidence for the biogenetic relationship between the typical cedrane and allo-cedrane sesquiterpenoids.
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Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Org Lett
Asunto de la revista:
BIOQUIMICA
Año:
2024
Tipo del documento:
Article
Pais de publicación:
Estados Unidos