Total Syntheses of (−)‐Secologanin, (−)‐5‐Carboxystrictosidine, and (−)‐Rubenine

Autor:	Kenta Rakumitsu, Jukiya Sakamoto, Hayato Ishikawa
Rok vydání:	2019
Předmět:	010405 organic chemistry Stereochemistry Dihydropyran Organic Chemistry Enantioselective synthesis Epoxide Total synthesis General Chemistry 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Organocatalysis Michael reaction Fukuyama reduction Secologanin
Zdroj:	Chemistry – A European Journal. 25:8996-9000
ISSN:	1521-3765 0947-6539
DOI:	10.1002/chem.201902073
Popis:	The first enantioselective total syntheses of (-)-secologanin (1), (-)-5-carboxystrictosidine (2), and (-)-rubenine (3) were accomplished in 10, 9, and 14 steps, respectively. The key transformation in the synthesis of 1 was a sequential anti-selective organocatalytic Michael reaction/Fukuyama reduction/spontaneous cyclization to form an optically active dihydropyran ring. In addition, the secologanin tetraacetate (16), which is a potential key intermediate for the bioinspired divergent syntheses of monoterpenoid indole alkaloids, was prepared in gram-scale in seven steps. The total syntheses of 2 and 3, which are classified as glycosylated monoterpenoid indole alkaloids, were achieved through bioinspired transformations such as a diastereoselective Pictet-Spengler reaction, a site- and stereoselective epoxidation, and a site-selective epoxide ring-opening followed by a lactonization reaction.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9f8857e0c6caa235b85971b02251516e https://doi.org/10.1002/chem.201902073 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
Nepřihlášeným uživatelům se plný text nezobrazuje	K zobrazení výsledku je třeba se přihlásit.