1096711-41-9Relevant academic research and scientific papers
Synthetic studies related to MPC1001: Formation of a model epidithiodiketopiperazine
Wang, Lihong,Clive, Derrick L.J.
scheme or table, p. 1504 - 1506 (2012/03/27)
A tricyclic epidithiodiketopiperazine was prepared having structural features related to the antitumor antibiotic MPC1001. The method is based on the use of the sulfenylating agent p-MeC6H4S(O 2)SCH2OSiMe2
[[(tert-Butyl)dimethylsilyl]oxy]-methylGroup for sulfur protection
Wang, Lihong,Clive, Derrick L. J.
supporting information; experimental part, p. 1734 - 1737 (2011/06/09)
Aromatic and aliphatic thiols can be protected by reaction with t-BuMe 2SiOCH2Cl in DMF in the presence of a base (2,6-lutidine or proton sponge); the resulting t-BuMe2SiOCH2SR or t-BuMe2SiOCH2SAr are deprotected by sequential treatment with Bu4NF and I2 to give symmetrical disulfides. Another mode of deprotection involves reaction with a sulfenyl chloride; this process gives an unsymmetrical disulfide and was examined with Me(CH2) 11SCH2OSiMe2Bu-t and three sulfenyl chlorides.
Asymmetric synthesis of the ABC-ring system of the antitumor antibiotic MPC1001
Peng, Jianbiao,Clive, Derrick L. J.
experimental part, p. 513 - 519 (2009/06/06)
trans-4-Hydroxy-L-proline was converted into a tricyclic compound representing three contiguous rings of the anticancer antibiotic MPC1001. The tricyclic model contains the dihydrooxepin and diketopiperazine subunits, as well as one of the sulfur atoms of the natural product. The diketopiperazine unit was formed by a new method that involves cyclization of an enolate onto the carbonyl of a phenyl carbamate, and the dihydrooxepin ring was generated by using an acid-induced cyclization of an alcohol onto the β-carbon of a vinylogous amide.
