Synthesis of prostaglandin-F2? by conjugate addition of a cuprate reagent to 3-t-butyldimethylsilyloxytricyclo[3.2.0.02,7]heptan-6-one

Bicyclo[3.2.0]carbocyclic Molecules and Redox Biotransformations: The Evolution of Closed-Loop Artificial Linear Biocatalytic Cascades and Related Redox-Neutral Systems

“…Samples of both recovered alcohols were also treated with N-bromosuccinamide to yield the corresponding complementary enantiomeric bromohydrins, analysis of which suggested that the enantiomeric purities of the corresponding endoand exo-alcohols were 88% and 84%, respectively. In turn, both bromohydrins could then serve as synthons for the subsequent synthesis of the nature-equivalent prostaglandin PGF2 α by two established enantiomer-specific routes [82,83]. Although this overall chemoenzymatic strategy achieved a successful outcome, it was stymied by two principal issues.…”

“…It was further reported that the activity of the aliquots of BSADH extract reclaimed from the various stopped reaction mixtures was approximately 70% of the originally prepared cell-free extract. Despite these various interesting outcomes and the long-established value of both chiral bicyclo[3.2.0]heptenones and corresponding heptenols as synthons for further chemocatalytic elaboration [82,83,[108][109][110], no further developments of this intriguing BSADH system have ever been reported in the scientific literature. After nearly two decades of investigations, commencing in 1979 with the Glaxo Group Research studies, it was apparent to the researchers at the University of Ferrara that no efficient biocatalytic means of generating enantiomerically pure 6-exo-bicyclo-[3.2.0]alkenols from the corresponding (rac)-alkenones had yet been reported.…”

Synthesis of Stilbenes Promoted by the Mixture of Zinc and Iron Powder

“…However, these methods have limitations. [14][15][16][17] Recently more efficient methods for the preparation of carboncarbon double bonds have been developed.1 8 Using metallic reagent, such as Pd,19-20 Cd,21 Zn,22-25 Zn-Cu couple. 26 These involve only one step, and the experimental procedure was significantly simplified.…”