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首页> 外文期刊>Chemistry: A European journal >Total Synthesis and Biological Evaluation of (+)-Neopeltolide and Its Analogues
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Total Synthesis and Biological Evaluation of (+)-Neopeltolide and Its Analogues

机译：（+）-新邻苯二酚及其类似物的全合成，生物学评价

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摘要

The stereocontrolled total synthesis of the originally proposed (1) and correct (2) structures of (+)-neopeltolide, a novel marine macrolide natural product with highly potent anti-proliferative activity against several cancer cell lines as well as potent antifungal activity, has been achieved by exploiting a newly developed Suzuki-Miyaura coupling/ring-closing metathesis strategy. Alkylborate 44, which was generated in situ from iodide 34, was coupled with enol phosphate 8 by a Suzuki-Miyaura coupling. Ring-closing metathesis of the derived diene 45 followed by stereoselective hydrogenation afforded tetrahydropyran 47 as a single stereoisomer in high overall yield from 34. Our convergent strategy enabled us to construct the 14-membered macrolactone core structure of 2 in a rapid and efficient manner. Total synthesis and biological evaluation of synthetic intermediates and designed synthetic analogues, performed to establish the structure-activity relationships of 2, led to the discovery of a structurally simple yet potent cytotoxic analogue, 9-demethylneopeltolide (54).
机译：（+）-neopeltolide（一种新的海洋大环内酯天然产物，对多种癌细胞具有高度有效的抗增殖活性以及有效的抗真菌活性）的最初提出的（1）和正确的（2）结构的立体控制的全合成具有通过开发新开发的Suzuki-Miyaura偶联/环闭合复分解策略来实现。由碘化物34原位产生的烷基硼酸酯44通过Suzuki-Miyaura偶合与烯醇磷酸酯8偶合。衍生二烯45的闭环易位反应，然后进行立体选择性氢化，从34上以较高的总收率得到四氢吡喃47，为单一的立体异构体。我们的聚合策略使我们能够快速有效地构建2的14元大内酯核心结构。为建立2的构效关系，对合成中间体和设计的合成类似物进行了全合成和生物学评估，从而发现了结构简单但有效的细胞毒性类似物9-demethylneopeltolide（54）。

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