1,3-Oxazine as a chiral building block used in the total synthesis of (+)-1-deoxynojirimycin and (2R,5R)-dihydroxymethyl-(3R,4R)-dihydroxypyrrolidine

Autor:	Ji-Yeon Kim, Seok-Hwi Park, Won-Hun Ham, Jin-Seok Kim, Changyoung Jung, Dong-Keun Song
Rok vydání:	2015
Předmět:	chemistry.chemical_classification Nucleophilic addition Stereochemistry Organic Chemistry Block (permutation group theory) Total synthesis Aldehyde Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry Yield (chemistry) Physical and Theoretical Chemistry 1-Deoxynojirimycin
Zdroj:	Tetrahedron: Asymmetry. 26:657-661
ISSN:	0957-4166
DOI:	10.1016/j.tetasy.2015.05.008
Popis:	Concise and stereocontrolled syntheses of (+)-1-deoxynojirimycin and (2R,5R)-dihydroxymethyl-(3R,4R)-dihydroxypyrrolidine [(+)-DMDP] were achieved via a diastereomerically enriched oxazine intermediate. The key strategies include the use of 1,3-oxazine as a chiral building block and diastereoselective nucleophilic addition to an aldehyde. Starting from readily available (R)-methyl 2-benzamido-3-((tert-butyldimethylsilyl)oxy)propanoate, (+)-1-deoxynojirimycin was synthesized in 11 steps and 26.2% overall yield while (+)-DMDP was synthesized in 11 steps and 27.1% overall yield, respectively.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::bead7d8478f00d81935f280c900cd69d https://doi.org/10.1016/j.tetasy.2015.05.008 Zobrazit plný text záznamu Full Text from ScienceDirect