Practical formal synthesis of D-(+)-biotin from 4-formylazetidin-2-one

TitlePractical formal synthesis of D-(+)-biotin from 4-formylazetidin-2-one
Publication TypeJournal Article
Year of Publication2007
AuthorsKale, AS, Puranik, VG, Deshmukh, ARakeeb A
JournalSynthesis-Stuttgart
Issue8
Pagination1159-1164
Date PublishedAPR
Type of ArticleArticle
ISSN0039-7881
Keywordsazetidin-2-one, beta-Lactams, cyclization, Lactone, reduction
Abstract

A practical synthesis of (3S,6R)-1,3-dibenzyltetrahydro-1H-furo[3,4-d]imidazole-2,4-dione, an important intermediate in the synthesis of biotin, from 4-formyl-3-mesyloxyazetidin-2-one has been achieved. Acid-catalyzed azetidin-2-one ring opening followed by a one-pot conversion of diamine hydrochloride to a cyclic urea and hydroxymethylene to chloromethylene by triphosgene to obtain (4S,5R)-methyl-1,3-dibenzyl-5-chloromethyl-2-oxoimidazolidine-4-carboxyl ate is the key step in this synthesis.

DOI10.1055/s-2007-965992
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)2.651
Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry