Stereocontrolled synthesis of enantiopure anticancer cyclopentenone prostaglandin analogues: (?)- and (+)-TEI-9826 |
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Authors: | Remigiusz ?urawiński Maciej Mikina Marian Miko?ajczyk |
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Institution: | Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, Sienkiewicza 112, 90-363 ?ód?, Poland |
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Abstract: | The synthesis of both enantiomers of TEI-9826 has been accomplished in seven steps with an overall yield of 44% starting from diastereomeric camphor protected 3-(dimethoxyphosphoryl)methyl]-4,5-dihydroxycyclopent-2-enones. The key steps include a fully diastereoselective hydrogenation of the endocyclic carbon–carbon double bond in the cyclopentenone ring controlled with a chiral diol moiety and the conversion of the latter into a new transposed olefinic bond. |
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