Total synthesis of the proposed structure for pochonicine and determination of its absolute configuration

Autor:	Koji Matsuoka, Hiroyuki Koshino, Shunya Takahashi, Yujiro Kitamura, Teruhiko Nitoda, Hiroshi Kanzaki, Takemichi Nakamura, Aya Tsuchida
Rok vydání:	2013
Předmět:	Natural product Pyrrolizidine alkaloid Stereochemistry Organic Chemistry Absolute configuration Diastereomer Total synthesis Biochemistry chemistry.chemical_compound chemistry Glucosamine Intramolecular force Drug Discovery Pyrrolizidine
Zdroj:	Tetrahedron Letters. 54:1456-1459
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2013.01.015
Popis:	Pochonicine is a polyhydroxylated pyrrolizidine alkaloid with a powerful inhibitory activity against β- N -acetylglucosaminidases. The proposed structure for pochonicine and the three diastereomers concerning its C-1 and/or C-3 positions were synthesized from N -acetyl- d -glucosamine through construction of the pyrrolizidine skeleton by two intramolecular amino cyclizations as key steps. This synthetic study not only revised the structure of the natural product to the corresponding 1,3-di- epi -form but also determined the absolute configuration as 1 R , 3 S , 5 R , 6 R , 7 S , 7a R .
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::53f5f65e54d3604b29b1d797385c0c37 https://doi.org/10.1016/j.tetlet.2013.01.015 Zobrazit plný text záznamu Full Text from ScienceDirect