Synthesis of Medium-Sized 2,ω-cis-Disubstituted Cyclic Ethers by Reductive Cyclization of Hydroxy Ketones

被引：7

作者：

Hernandez-Torres, Gloria ^{[1
]}

Mateo, Julio ^{[1
]}

Colobert, Francoise ^{[2
]}

Urbano, Antonio ^{[1
]}

Carreno, M. Carmen ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ Modulo 01, C Francisco Tomas & Valiente 7, E-28049 Madrid, Spain

[2] Univ Strasbourg ECPM, Lab Synth & Catalyse Asymetr, UMR CNRS 7509, 25 Rue Becquerel, F-67087 Strasbourg 02, France

来源：

CHEMISTRYSELECT | 2016年 / 1卷 / 13期

关键词：

Isolaurepan; Lauthisan; Obtusan; oxocarbenium ions; reductive cyclization; NUCLEOPHILIC-SUBSTITUTION REACTIONS; HIGHLY STEREOSELECTIVE REACTIONS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; C-GLYCOSYLATION REACTIONS; CONCISE TOTAL-SYNTHESIS; OXOCARBENIUM IONS; ELECTROSTATIC INTERACTIONS; ANNONACEOUS ACETOGENINS; STEREOELECTRONIC MODEL; ASYMMETRIC-SYNTHESIS;

D O I：

10.1002/slct.201601161

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of 7-, 8- and 9-membered cyclic ethers isolaurepan, lauthisan and obtusan was achieved through the cis-stereoselective TMSOTf/Et3SiH promoted reductive cyclization of the corresponding saturated hydroxy ketones, available in three steps from commercial starting materials: oxirane opening with lithium acetylide, Rh-catalyzed conjugate addition of the terminal alkynes to the corresponding unsaturated ketones and triple bond hydrogenation.

引用

页码：4101 / 4107

页数：7

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