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

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 21期

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

页码：6718 / 6723

页数：6

共 50 条

[1] Total Synthesis of (+)-Pleuromutilin
Farney, Elliot P.
Feng, Sean S.
Schafers, Felix
Reisman, Sarah E.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (04) : 1267 - 1270
[2] Asymmetric Total Synthesis of Pleuromutilin
Nakajima, Masaya
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2018, 76 (03) : 257 - 258
[3] Design, synthesis, and antibacterial activity of pleuromutilin derivatives
Liu, Hui-xian
Yao, Wen-yu
Cui, Ge
Zhou, Jing
Yan, Hao
Guo, Hui
Wang, Yu-wei
Zhang, Yue
CHEMICAL BIOLOGY & DRUG DESIGN, 2024, 103 (06)
[4] Synthesis and synthetic chemistry of pleuromutilin
Fazakerley, Neal J.
Procter, David J.
TETRAHEDRON, 2014, 70 (39) : 6911 - 6930
[5] Synthesis of Pleuromutilin
Foy, Nicholas J.
V. Pronin, Sergey
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (23) : 10174 - 10179
[6] Total synthesis of structurally diverse pleuromutilin antibiotics
Goethe, Olivia
DiBello, Mikaela
Herzon, Seth B.
NATURE CHEMISTRY, 2022, 14 (11) : 1270 - +
[7] Synthesis and antibacterial activities of pleuromutilin derivatives
Zhang, Yuan Yuan
Xu, Ke Ping
Ren, Dan
Ge, Shao Rong
Wang, Yu Liang
Wang, Yu Zhong
CHINESE CHEMICAL LETTERS, 2009, 20 (01) : 29 - 31
[8] Synthesis and antibacterial activities of pleuromutilin derivatives
Yuan Yuan Zhang~a
ChineseChemicalLetters, 2009, 20 (01) : 29 - 31
[9] A modular and enantioselective synthesis of the pleuromutilin antibiotics
Murphy, Stephen K.
Zeng, Mingshuo
Herzon, Seth B.
SCIENCE, 2017, 356 (6341) : 956 - 959
[10] Synthesis and Antibacterial Activity of Novel Pleuromutilin Derivatives
Liu, Huixian
Xiao, Sui
Zhang, Depeng
Mu, Shuhua
Zhang, Lifang
Wang, Xiaoyang
Xue, Feiqun
BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2015, 38 (07) : 1041 - 1048

← 1 2 3 4 5 →