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Toward the total synthesis of luminamicin; an anaerobic antibiotic: construction of highly functionalized cis-decalin containing a bridged ether moiety.
The Journal of Antibiotics ( IF 3.3 ) Pub Date : 2018-Feb-01 , DOI: 10.1038/ja.2017.77
Hiroyasu Ando , Aoi Kimishima , Motoyoshi Ohara , Tomoyasu Hirose , Takanori Matsumaru , Hirokazu Takada , Keisuke Morodome , Takehiro Miyamoto , Akihiro Sugawara , Satoshi Ōmura , Toshiaki Sunazuka

Synthesis of a cis-decalin moiety, containing an oxa-bridged cis-decalin ring system (11-oxatricyclo(5.3.1.1,703,8)undecane), as a key intermediate of the total synthesis of luminamicin (1) was accomplished. One of the essential steps in our synthetic route is construction of a cis-decaline framework using a one-pot Michael addition-aldol reaction. Additionally, the bridged ether moiety was obtained by an intramolecular 1,6-oxa-Michael reaction of a conjugated aldehyde.

中文翻译:

迈向光合霉素的全合成;一种厌氧抗生素:含有桥联醚部分的高度功能化的顺式十氢化萘的构建。

顺式萘烷的部分的合成,含有氧杂桥顺式-十氢萘环系统(11杂三环(5.3.1。1,7 0 3,8)十一烷),如luminamicin的全合成的关键中间体(1 )完成。我们合成路线中的基本步骤之一是使用一锅迈克尔加成-醛醇缩合反应构建顺式-十氢萘骨架。另外,通过共轭醛的分子内1,6-氧杂-迈克尔反应获得桥连的醚部分。
更新日期:2017-07-29
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