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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).
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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.

Key words

hexacyclinic acid - intramolecular Tsuji–Trost reaction - Crimmins aldol - relay ring-closing metathesis - natural products

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2022-1809.
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Publication History

Received: 18 November 2022

Accepted after revision: 30 January 2023

Accepted Manuscript online:
30 January 2023

Article published online:
02 March 2023

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