Nadein Oleg N, Kornienko Alexander
Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, NM 87801, USA.
Org Lett. 2004 Mar 4;6(5):831-4. doi: 10.1021/ol049942p.
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]
结构新颖的环醇类化合物1-芳基-1-脱氧甘露庚糖醇F可由d-木糖高效制备，其中关环复分解反应（RCM）为关键步骤。利用γ-烷氧基烯酸酯的非对映选择性芳基铜酸盐加成反应，可在环醇骨架中引入各种芳基残基，并实现完全的立体化学控制。该合成路线为抗肿瘤生物碱 pancratistatin及其芳基类似物的实际合成奠定了坚实基础。[结构：见正文]
