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Synthesis 2023; 55(15): 2333-2342
DOI: 10.1055/a-2022-1809
DOI: 10.1055/a-2022-1809
paper
Special Issue dedicated to Prof. David A. Evans
Synthesis of the CDF Ring System of Hexacyclinic Acid
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 productsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2022-1809.
- Supporting Information
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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