A new efficient synthesis of (S)-dolaphenine ((S)-2-phenyl-1-(2-thiazolyl)ethylamine), the C-terminal unit of dolastatin 10

Autor:	Naoko Irako, Yasumasa Hamada, Takayuki Shioiri
Rok vydání:	1992
Předmět:	Acylation Dolaphenine chemistry.chemical_compound chemistry Stereochemistry Organic Chemistry Drug Discovery Mitsunobu reaction Reaction intermediate Terminal unit Ethylamine Biochemistry Chemical synthesis
Zdroj:	Tetrahedron. 48:7251-7264
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(01)88264-8
Popis:	Four methods for the preparation of (S)-dolaphenine ((S)-2-phenyl-1-(2-thiazolyl)ethylamine, 2), which constitutes the C-termina unit of dolastatin 10 (1) having strong anticancer activity, has been investigated. Of these, the most efficient one involved the acylation of 2-lithiothiazole with N-methoxy-N-methylphenylacetamide (8), asymmetric reduction with (+)-diisopinocampheylchloroborane (11g), followed by the modified Mitsunobu reaction utilizing diphenyl phosphorazidate.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::de3ea9f732435204ce7f3e5906eda800 https://doi.org/10.1016/s0040-4020(01)88264-8 Zobrazit plný text záznamu