1.
Org Lett
; 2(23): 3719-21, 2000 Nov 16.
Article
in English
| MEDLINE
| ID: mdl-11073684
ABSTRACT
Methyl thiophene-2-carboxylate, methyl 3-(thien-2-yl)acrylate, and methyl 5,2'-bithiophene-2-carboxylate were utilized as the synthetic equivalents of pentanoate 5-anion, pentanoate 4,5-dianion, heptanoate 7-anion, and nonanoate-8,9-dianion. By the promotion of samarium diiodide, these thiophene-incorporating compounds reacted with aldehydes, ketones, and conjugated esters regioselectively at the thienyl rings. Long-chain esters with remote hydroxyl and carboxyl groups, including an antiarthritis agent, a shellac component, and an inhibitory agent of spore germination, were prepared after reductive desulfurization on Raney nickel.