Some aspects of intramolecular carbocyclization of methyl (2E)-3-[(1S,2R,5R)-2-({[tert-butyl(dimethyl)-silyl]oxy}methyl)-5-(trimethylsilyl)cyclopent-3-en-1-yl]prop-2-enoate and its derivatives

Development of a new approach for the synthesis of (+)-15-deoxy-Δ12,14-prostaglandin J2 methyl ester based on the [2+2]-cycloadduct of 5-trimethylsilylcyclopentadiene and dichloroketene

“…We considered two possible pathways to reach the synthetic equivalent of A. Thus, lactol 12 was formed by reduction with DIBAL-H in a high yield, 21 while treatment with lithium aluminum hydride led to diol 13 16,22 (Scheme 4). The use of DIBAL-H seemed more rational, since a latent aldehyde group was immediately formed at the center of the a-chain formation.…”