Development of Pd(OAc)2-catalyzed tandem oxidation of C N, C C, and C(sp3)–H bonds: Concise synthesis of 1-aroylisoquinoline, oxoaporphine, and 8-oxyprotoberberine alkaloids

Autor:	Saeko Nishimoto, Masahiro Toyota, Hiromichi Nakahashi
Rok vydání:	2020
Předmět:	Tandem 010405 organic chemistry Chemistry Organic Chemistry Liriodenine Total synthesis Alcohol 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Yield (chemistry) Drug Discovery Xylopinine Papaveraldine
Zdroj:	Tetrahedron Letters. 61:152599
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2020.152599
Popis:	A catalytic tandem oxidation of C N, C C, and C(sp3)–H bonds is developed. This tandem oxidation is applied to two-step total syntheses of papaveraldine and pulcheotine A. Additionally, the total synthesis of liriodenine is achieved in six steps from homopiperonyl alcohol and 2-bromophenylacetonitrile by applying this catalytic tandem oxidation. Moreover, the direct conversion of xylopinine to 8-oxypseudopalmatine in a 76% yield demonstrates the versatility of this catalytic reaction.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::89352dcaaa2ec0ee17f1cc4b25eecca1 https://doi.org/10.1016/j.tetlet.2020.152599 Zobrazit plný text záznamu Full Text from ScienceDirect