Synthesis of 8-R-9c-alkyl-1-aryl-2-benzyl-1-hydroxy-1,2,9b,9c-tetrahydro-5-oxa-2-aza-cyclopenta[2,3]cyclopropa[1,2-a]-naphthalene-3,4-diones and reaction thereof with acetic anhydride

The reaction of zinc enolates synthesized from 1-aryl-2,2-dibromoalkationes and zinc with 6-R-2-oxochromene-3-carboxylic acid N-benzylamide affords 8-R-9c-alkyl-1-aryl-2-benzyl-1-hydroxy-1,2, 9b,9c-tetrahydro-5-oxa-2-aza-cyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones. Acylation of these compounds is accompanied by an unexpected rearrangement producing a sole geometrical isomer of 4'-alkyl-5'-aryl-1'-benzyl-3,4,2',3'-tetrahydro-2,2'-dioxospiro[chroman-3,3'-pyrrol]-4-yl acetates. (c) 2005 Elsevier Ltd. All rights reserved.