Practical formal synthesis of D-(+)-biotin from 4-formylazetidin-2-one
Title | Practical formal synthesis of D-(+)-biotin from 4-formylazetidin-2-one |
Publication Type | Journal Article |
Year of Publication | 2007 |
Authors | Kale, AS, Puranik, VG, Deshmukh, ARakeeb A |
Journal | Synthesis-Stuttgart |
Issue | 8 |
Pagination | 1159-1164 |
Date Published | APR |
Type of Article | Article |
ISSN | 0039-7881 |
Keywords | azetidin-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. |
DOI | 10.1055/s-2007-965992 |
Type of Journal (Indian or Foreign) | Foreign |
Impact Factor (IF) | 2.651 |
Divison category:
Center for Material Characterization (CMC)
Organic Chemistry