184697-61-8Relevant academic research and scientific papers
Application of Dehydroabietic Acid in Palladium-Catalysed Enyne Cycloisomerisation
Wu, Na,Li, Ruikun,Cui, Feihu,Pan, Yingming
supporting information, p. 2442 - 2447 (2017/07/22)
Dehydroabietic acid (DAA) promotes palladium(0)-catalysed cyclisations of arene-tethered 1,7-enynols and 1,m-enynoates (m=6,7) to give fused carbocyclic dienes. 6,6,6,5-Tetracyclic lactones are accessible by one-pot cycloisomerisation/Diels–Alder reaction
Palladium-catalyzed intramolecular carboesterification of olefins
Li, Yang,Jardine, Katherine J.,Tan, Runyu,Song, Datong,Dong, Vy M.
, p. 9690 - 9692 (2010/04/28)
One catalyst three bonds: The title reaction between propiolic acids and unactivated olefins (see scheme; O red, Cl green) results in vicinal functionalization of the olefin, with the formation of new C-C and C-O bonds. Structurally complex 6,7,5-tricyclic ring systems are formed in a single step by this cascade chloropalladation and formal [3+2] cycloaddition.
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.
