Towards the total synthesis of pamamycin-607:: Preparation of the eastern part-(C8-C18 fragment)

被引：0
|
作者：
Mandville, G [1 ]
Bloch, R [1 ]
机构：
[1] Univ Paris Sud, Inst Chim Mol Orsay, CNRS, Lab Carbocycles,CNRS, F-91405 Orsay, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 1999卷 / 09期
关键词：
pamamycins; retro Diels-Alder reaction; 2,5-disubstituted tetrahydrofurans; reductive amination; intramolecular Michael cyclization;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Pamamycin-607 belongs to a group of homologous macrodiolides, produced by various "Streptomyces", that possess remarkable autoregulatory antifungal, antibacterial and anion-transfering activities. The synthesis of the nonracemic C-8-C-18 portion of pamamycin-607 is reported here and involves a route that features a stereoselective aldol condensation followed by a stereocontrolled reductive amination of the aldol and a cis-selective tetrahydrofuran formation by an intramolecular Michael cyclization induced by the geometry of the substrate.
引用
收藏
页码：2303 / 2307
页数：5
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