1295568-44-3Relevant articles and documents
Extending the utility of the bartoli indolization: Synthesis of marinoquinolines C and e
Lindsay, Ashleyc.,Sperry, Jonathan
, p. 461 - 464 (2013)
A short synthesis of marinoquinolines C and E has been achieved. The synthetic route involves an ipso nitration of an electron-deficient boronic acid, the first example of a Bartoli indolization on a nitroquinoline and Suzuki coupling between 2-chloropyrroloquinoline and two separate MIDA boronates. Georg Thieme Verlag Stuttgart · New York.
Total Syntheses of the 3 H-Pyrrolo[2,3- c]quinolone-Containing Alkaloids Marinoquinolines A-F, K, and Aplidiopsamine A Using a Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Pathway
Banwell, Martin G.,Bolte, Benoit,Bryan, Christopher S.,Fraser, Nicholas J.,Jackson, Colin J.,Kendrick, Amy,Lan, Ping,Rihouey, Charly,Sayyahi, Soheil,Sharp, Phillip P.,Ward, Jas S.,Willis, Anthony C.
, (2019/12/30)
Compounds 1-6 and 11 representing key members of the marinoquinoline family of natural products, together with the related marine alkaloid aplidiopsamine A (12), have been synthesized using various combinations of palladium-catalyzed Ullmann cross-coupling and reductive cyclization processes involving a C3-arylated pyrrole as the common intermediate. These natural products have been characterized by single-crystal X-ray analyses and evaluated as inhibitors of acetylcholinesterase (AChE) with congener 2 proving to be the most active.
Development of a Br?nsted acid-promoted arene-ynamide cyclization toward the total syntheses of marinoquinolines A and C and aplidiopsamine A
Yamaoka, Yousuke,Yoshida, Takahiro,Shinozaki, Makiko,Yamada, Ken-Ichi,Takasu, Kiyosei
, p. 957 - 964 (2015/03/05)
(Chemical Equation Presented) A Br?nsted acid-promoted arene-ynamide cyclization has been developed to construct the 3H-pyrrolo[2,3-c]quinolines. This reaction consists of the generation of a highly reactive keteniminium intermediate from arene-ynamide activated by a Br?nsted acid and electrophilic aromatic substitution reaction to give arene-fused quinolines in high yields. This methodology enabled facile access to marinoquinolines A and C and aplidiopsamine A.