REACTIONS OF ALPHA-ALKYL OR NO-ALKOXYCARBONYLMETHYLENE-(TRIPHENYL)PHOSPHORANES WITH PHENANTHRENE-9,1O-QUINONE - SYNTHESIS OF PHENANTHRO[9,1O-B]FURAN DERIVATIVES
Dn. Nicolaides et al., REACTIONS OF ALPHA-ALKYL OR NO-ALKOXYCARBONYLMETHYLENE-(TRIPHENYL)PHOSPHORANES WITH PHENANTHRENE-9,1O-QUINONE - SYNTHESIS OF PHENANTHRO[9,1O-B]FURAN DERIVATIVES, Journal of the Chemical Society. Perkin transactions. I, (15), 1994, pp. 2107-2112
Reactions of the alpha-methyl substituted title ylides 2a, 2b with qui
none 1 give the unexpected spiro-diastereoisomers 7 and 8 and the acry
lates 9. Reactions of the alpha-ethyl and alpha-benzyl substituted yli
des 2c and 2d with 1 afford compounds 4, 11 and 13, 14 respectively. R
eaction between 1 and the alpha-halogeno substituted ylides 2e, 2f lea
ds to formation of the diesters 16a and 16b respectively. All the fuse
d furan derivatives obtained are formed via an initial Wittig mono-ole
fination of 1 with the ylide used.