Total synthesis of marinomycins A-C and of their monomeric counterparts monomarinomycin A and iso-monomarinomycin A
Total synthesis of marinomycins A-C and of their monomeric counterparts monomarinomycin A and iso-monomarinomycin A
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DOI：
10.1021/ja068053p
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发表时间：
2007-02-14
影响因子：
15
通讯作者：
Yamaguchi, Junichiro
中科院分区：
文献类型：
--
作者：
Nicolaou, K. C.;Nold, Andrea L.;Yamaguchi, Junichiro
Marinomycins A-C（1-3）及其单体类似物monomarinomycin A（m-1）和iso-monomarinomycin A（m-2）通过会聚策略从关键结构单元酮膦酸酯5、醛6和二烯基溴羧酸7合成。首次尝试通过硼酸二烯基溴4的直接Suzuki型二聚/环化来构建marinomycin A [1，通过光可转化为marinomycin B（2）和C（3）]，导致过早闭环，在整体脱甲硅烷基化后，以良好的产率和仅少量（
Marinomycins A-C (1-3), and their monomeric analogues monomarinomycin A (m-1) and iso-monomarinomycin A (m-2), were synthesized by a convergent strategy from key building blocks ketophosphonate 5, aldehyde 6, and dienyl bromide carboxylic acid 7. The first attempt to construct marinomycin A [1, convertible to marinomycins B (2) and C (3 by light] by direct Suzuki-type dimerization/cyclization of boronic acid dienyl bromide 4 led to premature ring closure to afford, after global desilylation, monomarinomycin A (m-1) and iso-monomarinomycin A (m-2) in good yield and only small amounts (