Synlett 2022; 33(01): 48-51
DOI: 10.1055/a-1659-6521
cluster
Editorial Board Cluster

Diastereoselective Synthesis of the ABCD Ring System of Rubriflordilactone B

Hudson G. Roth
,
This project was supported by NSF-CAREER award CHE-1352490.


Zoom Image

Abstract

A novel nine-step diastereoselective route to the ABCD ring system of the natural product rubriflordilactone B is reported. Use of an α-substituted butenolide derived from maleic anhydride facilitated a 1,4-conjugate addition to provide a diene. The order in which a ring-closing metathesis and enolate oxidation were performed on this compound dictated the relative stereochemistry of the target. The final product exhibited anisotropic effects during room-temperature NMR studies, requiring elevated-temperature experiments to confirm its identity.

Supporting Information



Publikationsverlauf

Eingereicht: 10. September 2021

Angenommen nach Revision: 01. Oktober 2021

Accepted Manuscript online:
01. Oktober 2021

Artikel online veröffentlicht:
22. Oktober 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany