184697-62-9Relevant academic research and scientific papers
Synthesis of aromatic natural product frameworks using enyne metathesis
Rosillo, Marta,Casarrubios, Luis,Domínguez, Gema,Pérez-Castells, Javier
, p. 7029 - 7031 (2001)
Enynes, easily obtained by the Sonogashira coupling reactions of aromatic iodides, undergo, with good yields, enyne metathesis using the Grubbs catalyst. The resulting dienes are interesting carbo- and heterocycles which can give complex natural framework
Tandem Enyne Metathesis-Diels-Alder Reaction for Construction of Natural Product Frameworks
Rosillo, Marta,Dominguez, Gema,Casarrubios, Luis,Amador, Ulises,Perez-Castells, Javier
, p. 2084 - 2093 (2007/10/03)
Enynes connected through aromatic rings are used as substrates for metathesis reactions. The reactivity of three ruthenium carbene complexes is compared. The resulting 1,3-dienes are suitable precursors of polycyclic structures via a Diels-Alder process.
Acetylenic vinyllithiums: Consecutive cycloisomerization-[4 + 2] cycloaddition reactions
Bailey, William F.,Wachter-Jurcsak, Nanette M.,Pineau, Mark R.,Ovaska, Timo V.,Warren, Rachel R.,Lewis, Carl E.
, p. 8216 - 8228 (2007/10/03)
Acetylenic vinyllithiums (2), which were generated from the corresponding acetylenic vinyl bromides (3) by low-temperature lithium-bromine exchange, cyclize on warming to give, following quench with water, isomerically pure conjugated bis-exocyclic 1,3-dienes (1) in good to excellent yield. Both five-membered and six-membered outer-ring dienes may be prepared: 5-exo closure of an acetylenic vinyllithium, which proceeds with total stereocontrol via syn-addition to give the E-isomer of a five-membered outer-ring diene, tolerates aryl-, silyl-, or alkyl-substituents at the distal acetylenic carbon; the corresponding 6-exo process is less facile and seems to be confined to substrates bearing an anion-stabilizing substituent, such as phenyl or trimethylsilyl, at the terminal acetylenic carbon. The highly reactive bis-exocyclic 1,3-dienes serve as precursors to polycyclic materials through subsequent Diels-Alder reaction with a wide variety of dienophiles. The consecutive exchange-cyclization-cycloaddition methodology, which can be conducted in one pot without isolation of intermediates, provides an efficient, operationally simple, and diastereoselective route to diverse polycyclic ring systems.
