908003-67-8Relevant academic research and scientific papers
Pd-tBuONO Cocatalyzed Aerobic Indole Synthesis
Ning, Xiao-Shan,Liang, Xin,Hu, Kang-Fei,Yao, Chuan-Zhi,Qu, Jian-Ping,Kang, Yan-Biao
, p. 1590 - 1594 (2018)
A Pd-tBuONO co-catalyzed scalable and practical synthesis of indoles with molecular oxygen as terminal oxidant is developed. Either terminal or internal 2-vinylanilines could be smoothly converted to desired indoles under one general condition. This method has been evaluated in the large scale synthesis of indomethacin and a potential anti-breast cancer drug candidate 1. (Figure presented.).
New synthetic technologies for the construction of heterocycles and tryptamines
Nicolaou, K. C.,Krasovskiy, Arkady,Majumder, Utpal,Trepanier, Vincent E.,Chen, David Y.-K.
body text, p. 3690 - 3699 (2009/09/24)
New synthetic methods for the construction of novel heterocycles and tryptamines are described. Thus, N-Boc anilines (I) are sequentially converted to heterocycles II ((3-(2-aminophenyl)pyrrolidin-3-ol) derivatives),III (substituted 2-oxo-1,2-dihydrospirobenzo[d][1,3]oxazine-4,3'-pyrrol idines), and VI (2-(4,5-dihydro-1H-pyrrol-3-yl)aniline) derivatives through a route involving t-BuLi induced ortho-metalation/ LaCl3 2LiCl metalexchange, reaction with N-Boc pyrrolidin-3-one (5), and subsequent deca rboxylative fragmentation. Labile intermediates VI are effectively converted to tryptamines Xa and Xb under controlled proticacidconditions.Inadditiontoprovidingexpedientaccesstothe2-oxo- 1,2-dihydrospirobenzo[d][1,3]oxazine-4,3'-pyrrolidines (III), the method is applicable to the synthesis of the corresponding 2-oxo-1,2-dihydrospirobenzo[d] [1,3]oxazine-4,3'-piperidine series of spirocycles (e.g., 42) and their precursors (3-(2-aminophenyl)piperidin-3-ol derivatives, e.g., 43) by using N-Boc-protected piperidin-3-one (40). Applications of the developed synthetic technologies to the synthesis of regioisomeric spirocycles 87 and 90, tryptamines 88 and 91, Corey's aspidophytine tryptamine (97), and efavirenz (1) are also described.
Total synthesis of the alkaloid (±)-aspidophytine based on carbonyl ylide cycloaddition chemistry
Mejia-Oneto, Jose M.,Padwa, Albert
experimental part, p. 285 - 302 (2009/02/07)
The RhII-catalyzed cycloaddition cascade of an indolyl-substituted α-diazo imide was used for the total synthesis of the complex pentacyclic alkaloid (±)-aspidophytine. Treatment of the resulting dipolar cycloadduct with BF3·OEt
Application of the Rh(II) cyclization/cycloaddition cascade for the total synthesis of (±)-aspidophytine
Mejia-Oneto, Jose M.,Padwa, Albert
, p. 3275 - 3278 (2007/10/03)
A new strategy for the synthesis of (±)-aspidophytine has been developed and is based on a Rh(II)-catalyzed cyclization/dipolar cycloaddition sequence. The resulting [3+2]-cycloadduct undergoes an efficient Lewis acid mediated cascade that rapidly provide
