Synthese des tricyclo-[4.4.3.0]-tridecan

Chemo‐ and diastereoselective synthesis of new oxa[3.3.3]propellane via a domino cascade four‐component reaction based on diketene

“…Mass spectra have been recorded on a FINNIGAN-MATT 8430 mass spectrometer operating at an ionization potential of 70 eV. 1 H NMR (400 and 500 MHz) and 13 C NMR (100 and 125 MHz) spectra have been provided using Bruker DRX-400 AVANCE and Bruker DRX-500 AVANCE spectrometers. IR spectra have been recorded as KBr pellets on a Bruker Tensor 27 spectrometer, Melting points were measured on an Electrothermal 9100 apparatus.…”

“…[11] Although, much later, in 1965, the first 'propellane was designed and constructed. [12,13] Various methods have been reported for the synthesis of propellanes including Diels-Alder reaction, [14] photochemical additions, [15] manganese [16] or palladium [17] catalysis, nucleophilic substitutions of 1,1,2,2-tetrasubstituted alkenes [18] and rearrangement of spiro-ketones. [19] These processes are based on the introduction of a third ring on the framework of a fused bicyclic structure.…”

Synthesis of propellane-containing natural products

“…[1][2][3][4][5][6] However, the first 'propellane by design' was synthesized much later, in 1965. 7,8 Their nomenclature was introduced shortly thereafter. In 1966, Bloomfield and Irelan reported a synthesis of [4.4.2]propellane (1) and used the term propellerane in this context, 9 but the editors did not accept this nomenclature 10 and the compound was reported as 9,10-dihydro-9,10-ethanonaphthalene.…”

“…Arai and co-workers' synthesis 48 of norsterepolide (32) also commences with a Diels-Alder reaction of 2-(bromomethyl)maleic anhydride (8) and diene 35 (Scheme 7). The cycloaddition produced the endo-products 34a and 34b in a ratio of 4.5:1, which was inconsequential since, after esterification, the compound was treated with potassium tert-butoxide to close the cyclopropane ring in 90% yield.…”

Chemo- and Regioselective 4CR Synthesis of Oxathiaaza[3.3.3]propellanes via Sequential C–S, C–N and C–O Bond Formation in a Single Pot

“…9 However, the first 'propellane by design' was synthesized much later, in 1965. 10,11 Since their discovery in 1965, these polycyclic structures have received attention by many research groups due to their extended use and challenging architecture. Significant research in the field of the synthesis of propellanes (about 100 papers) has been carried out by The synthesis of propellanes containing carbonyl groups is of great interest and the rearrangement of spiroketones 13 and Diels-Alder reactions 14 are used for their synthesis.…”