Synthese von Plagiochin A und B, zwei macrocyclische Bis(bibenzylether) ausPlagiochila acantophylla

Autor:	Mária Kajtár-Peredy, László Kametler, Borbála Vermes, György M. Keserü, Gabriella Mezey-Vándor, Mihály Nógrádi
Rok vydání:	1992
Předmět:	Wurtz reaction Williamson ether synthesis chemistry.chemical_compound chemistry Bromide Stereochemistry Aryl Organic Chemistry Diphenyl ether Wittig reaction Bibenzyl Ether Physical and Theoretical Chemistry
Zdroj:	Liebigs Annalen der Chemie. 1992:1239-1243
ISSN:	1099-0690 0170-2041
DOI:	10.1002/jlac.1992199201206
Popis:	Synthesis of Plagiochins A and B, Macrocyclic Bis(bibenzyl) Ethers from Plagiochila acantophylla Plagiochins A (1) and B (2), macrocyclic bis(bibenzyl) ethers with a 16-membered ring, are synthesized. The key steps are the Pd(0)-catalyzed C—C coupling of an areneboronic acid (18) with an aryl bromide with formation of a biphenyl (13), Ullmann ether synthesis of a diphenyl ether (23), Wittig reaction to connect the two components 13 and 23, and a modified Wurtz reaction to close the ring. The latter reaction is accompanied by an unusual transformation of a C-benzyloxy to a C-benzoyl group.
Databáze:	OpenAIRE
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