ISSN:
0170-2041
Keywords:
Ethers, bis(bibenzyl), cyclic
;
Plagiochins
;
Benzyloxy-benzoyl transformation
;
Plagiochila acantophylla
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of Plagiochins A and B, Macrocyclic Bis(bibenzyl) Ethers from Plagiochila acantophyllaPlagiochins 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1992199201206
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