168553-63-7Relevant articles and documents
From Aziridines to Oxazolines and Thiazolines: The Heterocyclic Route to Thiangazole
Wipf, Peter,Venkatraman, Srikanth
, p. 1 - 10 (2007/10/03)
Since its isolation in 1991, the polyazole natural product thiangazole has become a popular target for total synthesis due to its challenging array of heterocyclic segments and its reported potent antiviral activity. The synthetic activity toward thiangazole is reviewed and a novel approach that takes advantage of aziridine and oxazoline intermediates en route to thiazolines is presented.
A new synthesis of α-methylserine by nucleophilic ring-opening of N-sulfonyl aziridines
Wipf, Peter,Venkatraman, Srikanth,Miller, Chris P.
, p. 3639 - 3642 (2007/10/02)
Conversion of tritylated 2-methylglycidol to the corresponding aziridine occurs by Staudinger cyclization of the intermediate azido alcohol. After N-sulfonylation with Ses-Cl and ring-opening with benzyl alcohol, oxidation of the primary alcohol provides. N,O-bisprotected α-methylserine directly suitable for repetitive peptide synthesis. This sequence represents a general enantioselective protocol for the synthesis of α-methylserine and other α,α-disubstituted amino acids.