Tetrahedron

Studies in cuprate rearrangement and stannylcupration: Application to the stereo-and enantiospecific synthesis of a stannyldiene C 10–C 15 fragment of des-epoxy- …

…, P Le Ménez, I Berque, J Ardisson, A Pancrazi

Index: Fargeas, Valerie; Le Menez, Patrick; Berque, Isabelle; Ardisson, Janick; Pancrazi, Ange Tetrahedron, 1996 , vol. 52, # 19 p. 6613 - 6634

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Citation Number: 61

Abstract

Metallate rearrangements were performed on α-(carbamoyloxy) alkenyl stannanes 4 in high yields to prepare (±)-8a and (±)-8b via alkyl transfer but failed when stannyl and stannylvinyl transfers were attempted to give 10ab and 1ab after quenching with Mel. After we optimized conditions on dihydrofuran 13, a model study, the dihydrofuran 19 could deliver cuprate rearrangements, leading after methylation to the stannyl derivative 10 and the ...