@article { ISI:000246298900004, title = {Practical formal synthesis of D-(+)-biotin from 4-formylazetidin-2-one}, journal = {Synthesis-Stuttgart}, number = {8}, year = {2007}, month = {APR}, pages = {1159-1164}, publisher = {GEORG THIEME VERLAG KG}, type = {Article}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, 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.

}, keywords = {azetidin-2-one, beta-Lactams, cyclization, Lactone, reduction}, issn = {0039-7881}, doi = {10.1055/s-2007-965992}, author = {Kale, Ajaykumar S. and Puranik, Vedavati G. and Deshmukh, Abdul Rakeeb A. S.} }