Concise Enantiospecific, Stereoselective Syntheses of (+)-Crispine A and Its (−)-Antipode

Autor:	Ruifang Wang, Balázs Gyimóthy, Mahender Gurram, R. Jason Herr, Feryan Ahmed, Sang Q. Lam
Rok vydání:	2011
Předmět:	Biological Products Pictet–Spengler reaction Decarboxylation Stereochemistry Chemistry Organic Chemistry Total synthesis Stereoisomerism Isoquinolines Chemical synthesis Substrate Specificity Adduct Enantiopure drug Tyrosine Organic chemistry Stereoselectivity
Zdroj:	The Journal of Organic Chemistry. 76:1605-1613
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo102112k
Popis:	An enantiospecific and stereoselective total synthesis of the natural product (+)-crispine A has been demonstrated employing a Pictet-Spengler bis-cyclization reaction between commercially available (R)-(-)-methyl 2-amino-3-(3,4-dimethoxyphenyl)propanoate and 4-chloro-1,1-dimethoxybutane to preferentially provide the cis tricyclic adduct. Decarboxylation by a convenient two-step protocol provided the enantiopure natural product in three steps with an overall isolated yield of 32% from the amino acid. The unnatural antipode (-)-crispine A was similarly prepared in three steps from the commercially available (S)-(+)-amino acid.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::eed4bff5cb6871694b610b61d5fb6b07 https://doi.org/10.1021/jo102112k Zobrazit plný text záznamu