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. 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.
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.
