Tetrahedron p. 1199 - 1210 (1990)
Update date:2022-08-04
Topics:
Bock, Inge
Bornowski, Hans
Ranft, Andreas
Theis, Heinz
3-substituted furan systems can be obtained by alkylation of 3-lithium furans with various electrophiles in the presence of hexamethylphosphoric acid triamide in good yields. The 2- or 5-position of 3-methyl furan is blocked with high regio selectivity by silylation. After metalation and alkylation of the remaining free α-position and subsequent desilylation the 2,3- and 2,4-disubstituted furans are obtained. These methods are used to synthesize the naturally occuring compounds ursinanolide (2) and longifolin (4).
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Doi:10.1021/jm00234a012
(1976)Doi:10.1021/ja00428a002
(1976)Doi:10.1016/S0022-328X(03)00454-6
(2003)Doi:10.1002/ardp.19763090509
(1976)Doi:10.1002/cbic.201402000
(2014)Doi:10.1007/BF00757982
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