Asymmetric synthesis of highly functionalized tyrosine derivatives for the construction of bistetrahydroisoquinoline alkaloids

Autor:	Baohe Guan, Xuan Pan, Zhanzhu Liu, Enming Du
Rok vydání:	2018
Předmět:	010405 organic chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Total synthesis Methylation 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Dihydroquinone chemistry.chemical_compound chemistry Yield (chemistry) Drug Discovery Phenol Tyrosine
Zdroj:	Tetrahedron Letters. 59:3029-3032
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2018.07.003
Popis:	A novel and facile synthesis of l -5-hydroxy-2,4-methoxy-3-methylphenylalanine derivatives, which are the key coupling partners for the asymmetric total synthesis of natural bistetrahydroisoquinoline alkaloids, is realized starting from l -tyrosine with 17% overall yield. The synthesis has been carried out on a multigram scale featuring the following key steps: (a) transformation of phenol to dihydroquinone via salcomine-catalyzed oxidation followed by zinc-acetic acid reduction; (b) single TBS-protection of dihydroquinone; (c) Mitsunobu methylation of the newly generated phenolic hydroxyl group.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::080647f8125a2daf5740149292b30e31 https://doi.org/10.1016/j.tetlet.2018.07.003 Zobrazit plný text záznamu Full Text from ScienceDirect