171011-87-3Relevant 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.
Total Synthesis of (-)-Thiangazole and Structurally Related Polyazoles
Wipf, Peter,Venkatraman, Srikanth
, p. 7224 - 7229 (2007/10/03)
Thiangazole was reported to be an extremely potent, nontoxic inhibitor of HIV-1 in MT4 cell assays.By employing a strategy of selective oxazoline-thiazoline interconversions, we have accomplished a total synthesis of the natural product in 16 steps and 1.1percent overall yield from (S)-α-methylserine.This new methodology is especially useful for the preparation of analogs of thiangazole and structure-activity studies.Our preliminary biological testing of (-)-thiangazole revealed a high level of cytotoxicity that was considerably reduced in the oxazoline-containing analogs.
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.
