171504-69-1Relevant academic research and scientific papers
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.
Thiolysis of oxazolines: A new, selective method for the direct conversion of peptide oxazolines into thiazolines
Wipf, Peter,Miller, Chris P.,Venkatraman, Srikanth,Fritch, Paul C.
, p. 6395 - 6398 (2007/10/02)
A direct oxazoline→thiazoline conversion can be realized by thiolysis of oxazolines with H2S in methanol/triethylamine, followed by cyclodehydration with Burgess reagent. This protocol is high-yielding, chemoselective, and essentially free of r
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.
