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

作者：Kale Ajaykumar S; Puranik Vedavati G; Deshmukh Abdul Rakeeb A S^*

来源：Synthesis, 2007, (8): 1159-1164.

DOI：10.1055/s-2007-965992

• beta-lactams
• cyclization
• reduction
• lactone
• azetidin-2-one

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-carboxylate is the key step in this synthesis.

• 出版日期2007-4-18