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2270-40-8

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THE FACILE CONVERSION OF T-2 TOXIN AND NEOSOLANIOL INTO ANGUIDINE
T-2 Toxin (5) and neosolaniol (6) are readily converted into anguidine (1) by a procedure where deoxygenation at the C-8 position is achieved, after conversion of the 3-TBDMS ether 7 of neosolaniol (6) to the β-bromide 11 for reduction to the anguidine precursor 12.
Anderson, Derek W.,Black, Robin M.,Leigh, David A.,Stoddart, Fraser J.,Williams, Nancy E.
p. 2661 - 2664
(1987)
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Trichothecene degradation studies. 2. Synthesis of [13-14C]anguidine
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.
Roush, William R.,Russo-Rodriguez, Sandra
p. 598 - 603
(2007/10/02)

Trichothecene degradation studies. 3. Synthesis of 12,13-deoxy-12,13-methanoanguidine and 12-epianguidine, two optically active analogues of the epoxytrichothecene mycotoxin anguidine
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.
Roush, William R.,Russo-Rodriguez, Sandra
p. 603 - 606
(2007/10/02)

Reductive amination of 3-Ketoanguidin and Antitumor Activity of the Products
Amine-containing trichothecanes were prepared by reductive aminations of 3-ketoanguidin.In in vivo tests against P388 leukemia, most of them showed an improved activity compared to anguidin though their potency was decreased. 3-Ketoanguidin also produced some unexpected structures: oxazoline 5, dioxaline 7, and α-amino nitrile 13.
Kaneko, T.,Wong, H.,Howell, H. G.,Rose, W. C.,Bradner, W. T.,Doyle, T. W.
p. 958 - 960
(2007/10/02)

Total synthesis of the trichothecene mycotoxin anguidine
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Brooks,Grothaus,Mazdiyasni
p. 4472 - 4473
(2007/10/02)

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Chemical Properties

Melting Point: 162-164℃
Boiling Point: 471.204°C at 760 mmHg
Flash Point:2 °C
Density: 1.315g/cm³
Storage Temp.:2-8°C
Vapor Pressure: 0mmHg at 25°C
Refractive Index: 1.4790 (estimate)
PKA: 13.40±0.70(Predicted)
PSA: 94.59000
LogP: 1.12490

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