Stereoselective Synthesis of Highly Substituted O-Heterocycles via Matteson Homologation: A Ring-Closing Metathesis Approach

被引：2

作者：

Kinsinger, Thorsten ^{[1
]}

Schaefer, Patrick ^{[1
]}

Kazmaier, Uli ^{[1
]}

机构：

[1] Saarland Univ, Organ Chem 1, D-66123 Saarbrucken, Germany

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 18期

关键词：

PROTECTED SIDE-CHAIN; BORONIC ESTERS; NATURAL-PRODUCTS; RUCL2(=CHR)(PR(3))(2); DERIVATIVES; COMPLEXES; MACROLIDE; CATALYSTS;

D O I：

10.1021/acs.orglett.3c01099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Matteson homologations of chiral boronic esters with the aid of unsaturated nucleophiles are powerful for gaining access to a range of different O-heterocycles via subsequent ring-closing metatheses. Using this protocol, six-to eight-membered rings become available and almost any position of the ring can be substituted and/or functionalized.

引用

页码：3303 / 3307

页数：5

共 50 条

[21] Synthesis of Substituted Aromatic Compounds Using Ruthenium-Catalyzed Ring-Closing Metathesis
Yoshida, Kazuhiro
Imamoto, Tsuneo
Yanagisawa, Akira
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2009, 67 (09) : 876 - 888
[22] Total synthesis of cyclic diterpene tonantzitlolone based on a highly stereoselective substrate-controlled aldol reaction and ring-closing metathesis
Jasper, Christian
Adibekian, Alexander
Busch, Torsten
Quitschalle, Monika
Wittenberg, Ruediger
Kirschning, Andreas
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (34) : 8719 - 8734
[23] Synthesis of highly functionalized cyclooctenes by ring-closing metathesis:: Unexpected formation of a trans isomer
Bourgeois, D
Pancrazi, A
Ricard, L
Prunet, J
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (04) : 725 - 728
[24] Design and synthesis of hetero-steroids via ring-closing metathesis: Biological studies towards in vitro anticancer activity
Kotha, Sambasivarao
Solanke, Balaji U.
Agarwala, Prema Kumari
Kapoor, Shobhna
STEROIDS, 2022, 188
[25] Diversity-Oriented Approach to Macrocyclic Cyclophane Derivatives via Ring-Closing Metathesis
Kotha, Sambasivarao
Shirbhate, Mukesh E.
SYNLETT, 2012, (15) : 2183 - 2188
[26] Two directional approach to spirocyclic ethers via Grignard reaction and ring-closing metathesis
Kotha, Sambasivarao
Ali, Rashid
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2016, 55 (09): : 1099 - 1106
[27] Synthesis of Dibenzoheteropines of Group 13-16 Elements via Ring-Closing Metathesis
Matsuda, Takanori
Sato, Shinya
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07): : 3329 - 3335
[28] Approach to the Synthesis of Briarane Diterpenes through a Dianionic Claisen Rearrangement and Ring-Closing Metathesis
Crimmins, Michael T.
Zhang, Yan
Williams, Philip S.
ORGANIC LETTERS, 2017, 19 (14) : 3907 - 3910
[29] A Ring-Closing Enyne Metathesis Approach to Functionalized Semicyclic Dienes: The Total Synthesis of (-)-Tetrangomycin
Moodie, Lindon W. K.
Larsen, David S.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (08) : 1684 - 1694
[30] Synthesis of a Ribose-Incorporating Medium Ring Scaffold via a Challenging Ring-Closing Metathesis Reaction
Rankin, Stuart S.
Caldwell, John J.
Cronin, Nora B.
van Montfort, Rob L. M.
Collins, Ian
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (26) : 4496 - 4507

← 1 2 3 4 5 →