STRIKING INFLUENCE OF THE REACTION CONDITIONS ON THE STEREOSELECTIVITY IN ELECTROPHILIC SUBSTITUTION OF A 10-LITHIO-ERGOLINYL-UREA

Article abstract of DOI:10.1016/S0040-4039(00)82364-3

The regioselectivity of the deprotonation of the 8α-ergolinyl-urea 1 (terguride) depends on the substituent at the indole nitrogen.A tert.-butyl-dimethylsilyl (TBDMS) protecting group facilitates the removal of the angular benzylic proton in position 10.The reaction of the 10-lithio compound 5 with electrophiles affords cis or trans fused products, depending on reagent and reaction conditions.