An improved approach to chiral cyclopentenone building blocks. Total synthesis of pentenomycin I and neplanocin A

被引：62

作者：

Gallos, JK ^{[1
]}

Stathakis, CI ^{[1
]}

Kotoulas, SS ^{[1
]}

Koumbis, AE ^{[1
]}

机构：

[1] Aristotle Univ Thessaloniki, Dept Chem, Thessaloniki 54124, Greece

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 17期

关键词：

D O I：

10.1021/jo050987t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An improved approach to enantiomerically pure hydroxylated cyclopentenones is reported here, which involves intramolecular nitrone cycloaddition of sugar-derived chiral pent-4-enals and hex-5-en-ones-2 followed by N-O bond cleavage, quaternization of the amine thus produced, and finally oxidative elimination of the amino group. Synthesis of pentenomycin I and neplanocin A is described following this methodology.

引用

页码：6884 / 6890

页数：7

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