Total Synthesis of (+)-Pleuromutilin

被引:70
|
作者
Fazakerley, Neal J. [1 ]
Helm, Matthew D. [1 ]
Procter, David J. [1 ]
机构
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
基金
英国工程与自然科学研究理事会;
关键词
natural products; pleuromutilin; radicals; samarium; total synthesis; ELECTRON-TRANSFER REDUCTION; SAMARIUM DIIODIDE; ORGANOZINC REAGENTS; SECONDARY ALCOHOLS; CARBONYL-COMPOUNDS; PLEUROMUTILIN; DERIVATIVES; ANTIBIOTICS; CHEMISTRY; IODIDE;
D O I
10.1002/chem.201300968
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first enantiospecific total synthesis of the antibacterial natural product (+)-pleuromutilin has been achieved. The approach includes the synthesis of a non-racemic cyclisation substrate from (+)-trans-dihydrocarvone, a highly selective SmI2-mediated cyclisation cascade, an electron transfer reduction of a hindered ester, and the first efficient conversion of (+)-mutilin to the target.
引用
收藏
页码:6718 / 6723
页数:6
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