97372-96-8Relevant academic research and scientific papers
CONVERSION OF ANGUIDINE INTO CALONECTRIN AND 3-DEACETYL-CALONECTRIN
Jeker, Nicolas,Mohr, Peter,Tamm, Christoph
, p. 5637 - 5640 (1984)
Anguidine (diacetoxyscirpenol, 2) was converted into calonectrin (3) in 7 steps using the Barton deoxygenation as key reaction.
Trichothecene degradation studies. 2. Synthesis of [13-14C]anguidine
Roush, William R.,Russo-Rodriguez, Sandra
, p. 598 - 603 (2007/10/02)
An efficient degradation and resynthesis of anguidine that pivots around norketone 4 is described. The sequence from anguidine to anguidine via 4 proceeds in 12 steps with an overall yield of 30%. This work has permitted for the first time the preparation of an enantiomerically pure, high specific activity 14C-labeled epoxytrichothecene mycotoxin required for biological investigations. The radiolabel was introduced by the reaction of 4 with [14C]CH2PPh3.
Trichothecene degradation studies. 3. Synthesis of 12,13-deoxy-12,13-methanoanguidine and 12-epianguidine, two optically active analogues of the epoxytrichothecene mycotoxin anguidine
Roush, William R.,Russo-Rodriguez, Sandra
, p. 603 - 606 (2007/10/02)
The title compounds were synthesized in order to further explore the apparent requirement of the trichothecene 12,13-epoxide unit for biological activity. Cyclopropane analogue 4 was prepared via a sequence involving a Simmons-Smith cyclopropanation of the anguidine degradation intermediate 6, whereas the key step in the synthesis of 12-epianguidine (5) was the dimethylsulfonium methylide mediated cyclopropanation of norketone 9. These compounds are among the first skeletally modified, semisynthetic trichothecene analogues to be prepared for biological evaluation.
