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Synthesis of the C(1)-C(11) polyene fragment of apoptolidin with a new sulfur dioxide-based organic chemistry

机译:基于新的基于二氧化硫的有机化学合成凋亡肽C(1)-C(11)多烯片段

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摘要

A new sulfur dioxide-based organic chemistry has been developed as a novel approach for the stereoselective synthesis of polyene fragments based on our one-pot, four-component synthesis of polyfunctional alpha-alkanesulfonyl-gamma,delta-unsaturated ketones. The flexibility and efficiency of this methodology are illustrated by the preparation of (+)-methyl (2E,4E,6E,8R,9S)-9-([(tert-butyl)dimethylsilyl]oxy}-2,4,6,8- tetramethyl-11-(triethylsilyl)undeca-2,4,6-trien-10-ynoate, a synthetic intermediate of Nicolaou and co-workers, that corresponds to the C(1)-C(11) fragment of apoptolidin, which was used by the authors in their total synthesis of this promising anticancer agent.
机译:一种新的基于二氧化硫的有机化学已被开发为一种基于我们的多官能α-链烷磺酰基-γ,δ-不饱和酮的一锅四组分合成的立体选择性合成多烯片段的新方法。通过制备(+)-甲基(2E,4E,6E,8R,9S)-9-(([(叔丁基)二甲基甲硅烷基]氧基} -2,4,6, 8-四甲基-11-(三乙基甲硅烷基)undeca-2,4,6-trien-10-ynoate,是Nicolaou和同事的合成中间体,对应于细胞凋亡素的C(1)-C(11)片段,作者将其用于这种有希望的抗癌剂的全合成中。

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