Bicyclo[2.2.1]Heptane as Cyclopentane Precursor. Part 3¹. A Convenient Route to [3.3.3]Propellanes

Application of Sequential Ring‐Opening, and Ring‐Closing Metathesis or Ring‐Rearrangement Metathesis to Design Oxacycles and Azacycles

“…[3] A perusal of literature indicate that the synthetic paths leading to 1 and 2 is not a trivial task. Their assembly involve the usage of toxic reagents such as metal cyanides and also lengthy synthetic sequence [9a,b] . In this regard, we identified a readily available endo ‐nadic anhydride 4 as a useful alternative [9c] .…”

Occurrence, synthesis and applications of natural and designed [3.3.3]propellanes

“…60 Thus, the team claimed that the stereochemical misassignment in the reported work by Mundy et al would be the result of an inversion in Smith's NMR data and that their work allowed to resolve this uncertainty, 127 although this assertion is still being debated. 13 Efforts by Ghosh et al 128 to construct strained systems such as [3.3.3]propellanes revealed that easily accessible bicyclo [2.2.1]heptanes, such as the diketone 227, can serve as excellent precursors (Scheme 33). Diketone 227 was found to be very suitable to undergo potassium tert-butoxide-mediated ring closure to the highly functionalized [3.3.3]propellane 228.…”