Synthetic approach to cis and trans-decalins via Diels—Alder reaction and ring-closing metathesis as key steps: further extension to dioxapropellane derivative by ring-closing metathesis

Structural assignment of a bis-cyclopentenyl-β-cyanohydrin formedviaalkene metathesis from either a triene or a tetraene precursor

“…We were therefore interested to explore whether experimental conditions could be found that would allow for efficient formation of product (8). There is surprisingly little precedence for the use of RCM to form decalins via processes in which the ring junction is established in concert with the ring formation (Kotha et al, 2011;Minger & Phillips, 2002) and in the most pertinent prior art, Lautens showed that for his tetraene substrates, cis-3,4,5,6-dehydrodecalin products generally predominated over the trans congeners (Lautens & Zunic, 2004;Lautens & Hughes, 1999) However, Lautens' systems have no potentially competitive bis-cyclopentene pathway and the factors affecting the cis-trans ratios in his system were not considered to translate directly to ours.…”

Design and synthesis of hybrid cyclophanes containing thiophene and indole units via Grignard reaction, Fischer indolization and ring-closing metathesis as key steps

“…Analogously as described in [42], a solution of bisindole-alkene derivative 5 (0.05 mmol) in dry CH 2 Cl 2 (50 mL) was degassed with N 2 gas for 10 min. Then, Grubbs’ second generation catalyst (10 mol %) was added and the reaction mixture was stirred at room temperature for 24 h. After completion of the reaction (TLC monitoring), the solvent was removed under reduced pressure and the crude product was purified by silica gel column chromatography (5% EtOAc/petroleum ether) to give the RCM compound 1 as a colourless solid.…”

Design and Synthesis of Polycycles, Heterocycles, and Macrocycles via Strategic Utilization of Ring‐Closing Metathesis

“…A simple route to [8.4.4]dioxapropellane 161 was reported based on RCM . To this end, the required precursor 159 synthesis was accomplished using diethyl ester 157 involving a three‐step sequence.…”