Abstract
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 regioselectivity 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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