Synthetically attractive chiral cyclopentenone building blocks conjugated with tetrahydro- and 2-oxotetrahydrofurans

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.…”