1246523-61-4Relevant academic research and scientific papers
Total Synthesis of Dictyodendrins A–F by the Gold-Catalyzed Cascade Cyclization of Conjugated Diyne with Pyrrole
Inuki, Shinsuke,Matsuda, Yuka,Matsuoka, Junpei,Miyamoto, Yoichi,Ohno, Hiroaki,Oishi, Shinya,Oka, Masahiro,Otani, Mayumi
, (2020/07/13)
The total synthesis of dictyodendrins A–F was achieved by using the gold(I)-catalyzed annulation of a conjugated diyne with N-Boc-pyrrole for direct construction of the pyrrolo[2,3-c]carbazole scaffold. Late-stage functionalization of the resulting pyrrolo[2,3-c]carbazole to introduce various substituents provided divergent access to dictyodendrins. Some dictyodendrin analogues exhibited inhibitory activities toward CDK2/CycA2 and GSK3.
Total Synthesis of Dictyodendrins by the Gold-Catalyzed Cascade Cyclization of Conjugated Diynes with Pyrroles
Matsuoka, Junpei,Matsuda, Yuka,Kawada, Yuiki,Oishi, Shinya,Ohno, Hiroaki
, p. 7444 - 7448 (2017/06/13)
In total and formal syntheses of dictyodendrins B, C, E, and F, the key step involved the direct construction of the pyrrolo[2,3-c]carbazole core by the gold-catalyzed annulation of a conjugated diyne with a pyrrole to form three bonds and two aromatic rings. The subsequent introduction of substituents at the C1 (Suzuki–Miyaura coupling), C2 (addition to an aldehyde), N3 (alkylation), and C5 positions (Ullman coupling) provided divergent access to dictyodendrins.
A concise and scalable strategy for the total synthesis of dictyodendrin B based on sequential C-H functionalization
Pitts, Andrew K.,O'Hara, Fionn,Snell, Robert H.,Gaunt, Matthew J.
supporting information, p. 5451 - 5455 (2015/04/27)
A sequential C-H functionalization strategy for the synthesis of the marine alkaloid dictyodendrin B is reported. Our synthesis begins from commercially available 4-bromoindole and involves six direct functionalizations around the heteroarene core as part of a gram-scale strategy towards the natural product.
Total synthesis of dictyodendrins A-E
Tokuyama, Hidetoshi,Okano, Kentaro,Fujiwara, Hideto,Noji, Toshiharu,Fukuyama, Tohru
, p. 560 - 572 (2011/10/03)
A highly efficient total synthesis of dictyodendrins A-E was accomplished. The synthesis features a novel benzyne-mediated one-pot indoline formation/cross-coupling sequence for the construction of a highly substituted key indoline intermediate. Peripheral substituents were introduced onto this intermediate in a modular fashion to complete the total synthesis of dictyodendrins A-E. A benzyne-mediated one-pot indoline formation/cross-coupling sequence is used for the construction of a highly substituted common indole intermediate. The peripheral substituents were introduced using a Friedel-Crafts reaction on the indole intermediate in a modular fashion to complete the total synthesis. Copyright
Total synthesis of dictyodendrin A and B
Okano, Kentaro,Fujiwara, Hideto,Noji, Toshiharu,Fukuyama, Tohru,Tokuyama, Hidetoshi
supporting information; experimental part, p. 5925 - 5929 (2010/10/03)
(Figure Presented) In-do-line of fire: A highly efficient total synthesis of the title compounds features a novel benzyne-mediated one-pot indoline formation/cross-coupling sequence for the construction of a highly substituted key indoline intermediate. The peripheral substituents were then introduced onto the intermediate in a modular fashion to complete the total syntheses of dictyodendrin A and B.
