Stereoselective synthesis of the C5-C18 fragment of halichomycin.
Stereoselective synthesis of the C5-C18 fragment of halichomycin.
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DOI：
10.1021/jo202602n
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发表时间：
2012-04
期刊：
影响因子：
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通讯作者：
Qingjiang Li;S. Mao;Yu-xin Cui;Yanxing Jia
中科院分区：
文献类型：
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作者：
Qingjiang Li;S. Mao;Yu-xin Cui;Yanxing Jia
报道了一种高效、收敛的合成halichomycin的C(5)-C（18）片段的方法。通过催化剂控制，立体选择性地从(R)-罗氏酯制备了丁内酯片段6；通过底物控制，以(S)-丝氨酸为原料合成了二烯溴结构域7。C(5)-C（18）片段2通过丁内酯与二烯溴的立体选择性烷基化反应快速组装，随后进行官能团转化。
An efficient and convergent synthesis of the C(5)-C(18) fragment of halichomycin is reported. Butanolide fragment 6 was readily prepared stereoselectively from (R)-Roche ester through catalyst control; dienylic bromide domain 7 was synthesized from (S)-serine by substrate control. C(5)-C(18) fragment 2 was rapidly assembled through a stereoselective alkylation of the butanolide with the dienylic bromide, followed by functional group transformations.