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Synlett 2016; 27(16): 2345-2351
DOI: 10.1055/s-0035-1562511
DOI: 10.1055/s-0035-1562511
letter
Synthetic Study on Carthamin: Problem and Solution for Oxidative Dearomatization Approach to Quinol C-Glycoside
Weitere Informationen
Publikationsverlauf
Received: 30. April 2016
Accepted after revision: 31. Mai 2016
Publikationsdatum:
05. Juli 2016 (online)
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Abstract
Synthetic study on carthamin, a natural red pigment, is described. Attempts at the construction of the key quinol C-glycoside structure by oxidative dearomatization of C-glycosyl phenols were hampered by the competing cleavage of the C1–C2 bond in the sugar moiety. By employing the 2-O-acetyl protection, the projected reaction proceeded smoothly, giving the desired products in good to excellent yields. An interesting photochemical stability/instability of the chalcone geometry in the synthetic compounds was observed.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562511.
- Supporting Information
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References and Notes
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For contributions from our laboratory, see:
For reviews, see:
For early examples of the Friedel–Crafts C-glycosylation of phloroglucinol derivatives, see:
For related examples, see:
For the pertinent examples, see: