An approach to pancratistatins via ring-closing metathesis: efficient synthesis of novel 1-aryl-1-deoxyconduritols F. cv.
An approach to pancratistatins via ring-closing metathesis: efficient synthesis of novel 1-aryl-1-deoxyconduritols F. cv.
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DOI：
10.1021/ol049942p
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发表时间：
2004-01
期刊：
影响因子：
5.2
通讯作者：
O. N. Nadein;A. Kornienko
中科院分区：
文献类型：
--
作者：
O. N. Nadein;A. Kornienko
以d-木糖为原料，以RCM为关键步骤，高效地合成了结构新颖的环醇-1-芳基-1-脱氧-杜仲醇F。各种芳香族残基通过全立体化学控制结合到环醇骨架中，利用非对映选择性芳基铜酸盐与伽马-烷氧基烯醇酸酯的加成。该合成路线为抗肿瘤生物碱泛曲他汀及其芳基类似物的实际合成奠定了坚实的基础。[结构：见正文]
Structurally novel cyclitols, 1-aryl-1-deoxyconduritols F, were efficiently prepared from d-xylose, utilizing RCM as a key step. Various aromatic residues were incorporated in the cyclitol skeleton with total stereochemical control, utilizing a diastereoselective aryl cuprate addition to a gamma-alkoxy enoate. The synthetic route establishes a firm foundation for a practical synthesis of the antitumor alkaloid pancratistatin and its aryl analogues. [structure: see text]