Total Synthesis of the Hexacyclic Sesterterpenoid Niduterpenoid B via Structural Reorganization Strategy.
J Am Chem Soc
; 146(37): 25445-25450, 2024 Sep 18.
Article
em En
| MEDLINE
| ID: mdl-39235150
ABSTRACT
To date, it remains challenging to precisely and efficiently construct structurally intriguing polycarbocycles with densely packed stereocenters in organic synthesis. Niduterpenoid B, a naturally occurring ERα inhibitor, exemplifies this complexity with its intricate polycyclic network comprising 5 cyclopentane and 1 cyclopropane rings, featuring 13 contiguous stereocenters, including 4 all-carbon quaternary centers. In this work, we describe the first total synthesis of niduterpenoid B using a structural reorganization strategy. Key features include the following (1) an efficient methoxy-controlled cascade reaction that precisely forges a highly functionalized tetraquinane (A-D rings) bearing sterically hindered contiguous quaternary stereocenters; (2) a rhodium-catalyzed [1 + 2] cycloaddition that facilitates the construction of a strained 3/5 bicycle (E-F rings) angularly fused with ring D.
Texto completo:
1
Base de dados:
MEDLINE
Idioma:
En
Revista:
J Am Chem Soc
/
Journal of the american chemical society
/
J. am. chem. soc
Ano de publicação:
2024
Tipo de documento:
Article
País de afiliação:
China