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Synthesis 2021; 53(12): 2092-2102
DOI: 10.1055/s-0040-1706684
DOI: 10.1055/s-0040-1706684
paper
Stereoselective Convergent Synthesis of Carbon Skeleton of Cotylenin A Aglycone
This work was financially supported by the Japan Society for the Promotion of Science (JSPS KAKENHI Grant Numbers JP16K08180, JP18K14876, JP19K06981) and a Nagai Memorial Research Scholarship from the Pharmaceutical Society of Japan.
Abstract
In this paper, the synthesis of the carbon skeleton of cotylenin A aglycone is described. The key reactions, including an intramolecular aldol reaction, an aldol coupling reaction, and a ring-closing metathesis, allow for the effective and stereoselective access to the carbon skeleton of cotylenin A aglycone. The stereochemistry was confirmed by single-crystal X-ray crystallographic analyses of related compounds.
Key words
cotylenin A - cotylenol - carbocycles - polycycles - natural products - ring-closing metathesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706684.
- Supporting Information
Publication History
Received: 08 December 2020
Accepted after revision: 28 December 2020
Article published online:
01 February 2021
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14 CCDC 2048792 (18) and 2048793 (25) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures. A summary of the crystallographic analysis and the crystal structure is provided in the Supporting Information.
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15 The structure of dimer of 3 was inferred from crude MS and NMR spectroscopy.