Stereoselective synthesis of morphine fragments trans- and cis-octahydro-1H-benzo[4,5]furo[3,2-e]isoquinolines

Autor:	Li-Te Chang, Chia-Huei Hsu, Ling-Wei Hsin, Chien-Wei Chen, Hung-Wei Chen
Rok vydání:	2005
Předmět:	Carbamate Chemistry Stereochemistry medicine.medical_treatment Organic Chemistry Intramolecular cyclization Biochemistry Claisen rearrangement chemistry.chemical_compound Heck reaction Drug Discovery Chemical reduction Morphine medicine Stereoselectivity Isoquinoline medicine.drug
Zdroj:	Tetrahedron. 61:513-520
ISSN:	0040-4020
DOI:	10.1016/j.tet.2004.10.067
Popis:	A stereoselective synthesis of the ACNO partial structures of morphine has been developed. Palladium-catalyzed cyclization of carbamate 2 provided the tetracyclic (ACNO) 3-ethoxycarbonyl-9-methoxy-2,3,5,6,7,7a-hexahydro-1H-benzofuro[3,2-e]isoquinoline ( 14 ); while treatment of 5-(2-bromo-6-methoxyphenoxy)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline ( 8 ) under the same reaction condition gave 8a-(2-hydroxy-3-methoxyphenyl)-1,2,3,4,6,7,8,8a-octahydroisoquinoline ( 11 ) via an unusual Claisen rearrangement. 9-Methoxy-3-methyl-2,3,5,6,7,7a-hexahydro-1H-benzofuro[3,2-e]isoquinoline ( 7 ) was successfully transformed to trans-octahydroisoquinoline 3 and cis-octahydroisoquinoline 4 via catalytical hydrogenation over PtO2 and chemical reduction with acidic NaBH4, respectively.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::56c581dd05bb8cb6e15ed03be24cb77c https://doi.org/10.1016/j.tet.2004.10.067 Zobrazit plný text záznamu Full Text from ScienceDirect