Synthesis 2023; 55(15): 2333-2342
DOI: 10.1055/a-2022-1809
paper
Special Issue dedicated to Prof. David A. Evans

Synthesis of the CDF Ring System of Hexacyclinic Acid

Alexandre Audic
,
Joëlle Prunet
The University of Glasgow is acknowledged for financial support. The Engineering and Physical Sciences Research Council (EPSRC) provided a doctoral training allocation to A.A. (EP/K503058/1).


Abstract

Diverse approaches to prepare the nine-membered ring precursor of the DEF fragment of hexacyclinic acid are described, culminating in the synthesis of the CDF ring system of this natural product. The key steps are a Michael addition/elimination sequence and an original intramolecular Tsuji–Trost reaction of an enol with an allylic alcohol.

Supporting Information



Publikationsverlauf

Eingereicht: 18. November 2022

Angenommen nach Revision: 30. Januar 2023

Accepted Manuscript online:
30. Januar 2023

Artikel online veröffentlicht:
02. März 2023

© 2023. Thieme. All rights reserved

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