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
收藏
页码：6884 / 6890
页数：7
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