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

[11] Stereoselective synthesis of the naturally occurring lactones (-)-osmundalactone and (-)-muricatacine using ring-closing metathesis
Carda, M
Rodríguez, S
González, F
Castillo, E
Villanueva, A
Marco, JA
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (15) : 2649 - 2655
[12] Synthesis of macrocyclic natural products by catalyst-controlled stereoselective ring-closing metathesis
Yu, Miao
Wang, Chenbo
Kyle, Andrew F.
Jakubec, Pavol
Dixon, Darren J.
Schrock, Richard R.
Hoveyda, Amir H.
NATURE, 2011, 479 (7371) : 88 - 93
[13] An Approach to the Synthesis of Pyrimido[b]azepines via Ruthenium-Catalyzed Ring-Closing Metathesis
Zhang, Tong-Bo
Yang, Quan-Zhi
Cao, Yuan-Yuan
Wu, Shao-Tong
Zhang, Yu
Guo, Ying
Zhao, Jian-Xiong
Sun, Xue-Feng
Zhang, Zhi-Li
Tian, Chao
Liu, Jun-Yi
Wang, Xiao-Wei
SYNTHESIS-STUTTGART, 2015, 47 (21): : 3292 - 3300
[14] The Ruthenium-Catalyzed Domino Cross Enyne Metathesis/Ring-Closing Metathesis in the Synthesis of Enantioenriched Nitrogen-Containing Heterocycles
Llobat, Alberto
Escorihuela, Jorge
Sedgwick, Daniel M.
Rodenes, Miriam
Roman, Raquel
Soloshonok, Vadim A.
Han, Jianlin
Medio-Simon, Mercedes
Fustero, Santos
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (27) : 4193 - 4207
[15] Synthesis of substituted pyridines and pyridazines via ring closing metathesis
Donohoe, Timothy J.
Fishlock, Lisa P.
Basutto, Jose A.
Bower, John F.
Procopiou, Panayiotis A.
Thompson, Amber L.
CHEMICAL COMMUNICATIONS, 2009, (21) : 3008 - 3010
[16] Stereocontrolled Synthesis of the Highly Functionalized Core Structure of Aurisides by Ring-Closing Metathesis
Bourcet, Emmanuel
Fache, Fabienne
Piva, Olivier
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (21) : 4075 - 4087
[17] Stereoselective total synthesis of decarestrictine-J via Ring Closing Metathesis (RCM)
Yadav, J. S.
Lakshmi, K. Anantha
Reddy, N. Mallikarjuna
Prasad, Attaluri R.
Reddy, Basi V. Subba
TETRAHEDRON, 2010, 66 (01) : 334 - 338
[18] SYNTHETIC APPROACH TO OXA-CAGE SYSTEMS VIA RING-CLOSING METATHESIS
Kotha, Sambasivarao
Cheekatla, Subba Rao
Meshram, Milind
HETEROCYCLES, 2018, 97 (02) : 1008 - 1018
[19] Synthesis of Various Heterocycles Having a Dienamide Moiety by Ring-Closing Metathesis of Ene-ynamides
Wakamatsu, Hideaki
Sasaki, Yoshimi
Kawahata, Masatoshi
Yamaguchi, Kentaro
Yoshimura, Yuichi
SYNTHESIS-STUTTGART, 2018, 50 (17): : 3467 - 3486
[20] Novel Strategy for the Bis-Butenolide Synthesis via Ring-Closing Metathesis
Billamboz, Muriel
Legeay, Jean Christophe
Hapiot, Frederic
Monflier, Eric
Len, Christophe
SYNTHESIS-STUTTGART, 2012, 44 (01): : 137 - 143

← 1 2 3 4 5 →