Total synthesis of (+) methyl β-d-vicenisaminide

Autor:	Mikio Fujii, Machiko Ono, Taker U. Ehara, Hiroyuki Akita
Rok vydání:	2010
Předmět:	Stereochemistry Organic Chemistry Total synthesis Catalysis Stereocenter Inorganic Chemistry Benzaldehyde Base (group theory) chemistry.chemical_compound chemistry Nucleophile Intramolecular force Alkoxide Physical and Theoretical Chemistry Conjugate
Zdroj:	Tetrahedron: Asymmetry. 21:494-499
ISSN:	0957-4166
Popis:	The total synthesis of methyl β- d -vicenisaminide 1 has been achieved. In this approach, the synthesis of enantiomerically pure methyl (4 R ,5 S )- and (4 S ,5 R )-4-azido-5-hydroxy-2( E )-hexenoates 2 was established by enzymatic resolution of (±)- anti -5-acetoxy -4-azido-2( E )-hexenoate 4 . Another stereogenic center was introduced by base-catalyzed intramolecular conjugate addition of a hemiacetal-derived alkoxide nucleophile obtained by the reaction of methyl (4 S ,5 R )- N -4- tert -butoxycarbonyl- N -methylamino-5-hydroxyl-2( E )-hexenoate 8 and benzaldehyde in the presence of a base.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0155408c9d22e20926abb939f5ee2551 https://doi.org/10.1016/j.tetasy.2010.02.014 Zobrazit plný text záznamu Full Text from ScienceDirect