Ring-Closing Metathesis as Methodology for the Synthesis of 2-and 3-Arylbenzo[b]furans

被引：0

作者：

Visser, Melanie ^{[1
]}

Twigge, Linette ^{[1
]}

Marais, Charlene ^{[1
]}

Bezuidenhoudt, Barend C. B. ^{[1
]}

机构：

[1] Univ Free State, Dept Chem, POB 339, ZA-9300 Bloemfontein, South Africa

来源：

SYNTHESIS-STUTTGART | 2024年 / 56卷 / 22期

基金：

新加坡国家研究基金会;

关键词：

arylbenzofurans; metathesis; Grubbs catalyst; allylation; Tebbe methylenation; Grignard reagent; Al(OTf)(3); BIOACTIVE BENZOFURAN DERIVATIVES; CYCLIC ENOL ETHERS; CLAISEN REARRANGEMENT; CONVENIENT SYNTHESIS; EFFICIENT SYNTHESIS; CARBONYL-COMPOUNDS; PHENOLS; LITHIATION; REAGENT; ACID;

D O I：

10.1055/a-2367-2151

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Olefin metathesis, which is well established in the petrochemical industry, is also emerging as a green technology in the manufacture of pharmaceutical and specialty chemicals. Arylbenzofurans are of interest for potential medicinal applications. In this paper we report on the synthesis of various 2-aryl- and 3-arylbenzo[ b ]furans with natural substitution patterns from readily available starting materials in a strategy that applies ring-closing metathesis with the Grubbs second generation catalyst as key step.

引用

页码：3488 / 3502

页数：15

共 50 条

[1] A ring-closing metathesis approach to a synthesis of the B ring of eleutherobin
Kaliappan, KP
Kumar, N
TETRAHEDRON LETTERS, 2003, 44 (02) : 379 - 381
[2] Synthesis of coumarins by ring-closing metathesis
Chatterjee, AK
Toste, FD
Goldberg, SD
Grubbs, RH
PURE AND APPLIED CHEMISTRY, 2003, 75 (04) : 421 - 425
[3] Synthesis of Sultams by Ring-Closing Metathesis
Mondal, Shovan
Debnath, Sudarshan
SYNTHESIS-STUTTGART, 2014, 46 (03): : 368 - 374
[4] Ring-closing metathesis as a new methodology for the synthesis of monomeric flavonoids and neoflavonoids
Miller, Bradley J.
Pieterse, Tanya
Marais, Charlene
Bezuidenhoudt, Barend C. B.
TETRAHEDRON LETTERS, 2012, 53 (35) : 4708 - 4710
[5] Synthesis of (+)-didemniserinolipid B via ketalization/ring-closing metathesis
Marvin, Christopher C.
Voight, Eric A.
Burke, Steven D.
ORGANIC LETTERS, 2007, 9 (26) : 5357 - 5359
[6] Total synthesis of aspinolide B: a ring-closing metathesis approach
Ghosh, Subhash
Rao, R. Vengal
TETRAHEDRON LETTERS, 2007, 48 (39) : 6937 - 6940
[7] Synthesis of thromboxane B2 via ketalization/ring-closing metathesis
Marvin, Christopher C.
Clemens, Alexander J. L.
Burke, Steven D.
ORGANIC LETTERS, 2007, 9 (26) : 5353 - 5356
[8] A ring-closing metathesis approach for the synthesis of (±)-pregabalin
Vivek D. Bobade
Pravin C. Mhaske
Kamlesh S. Vadgaonkar
Shivaji H. Shelke
Monatshefte für Chemie - Chemical Monthly, 2012, 143 : 847 - 851
[9] Synthesis of cyclic peptides by ring-closing metathesis
Reichwein, JF
Versluis, C
Liskamp, RMJ
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19): : 6187 - 6195
[10] Synthesis of the mycolactone core by ring-closing metathesis
Alexander, Matthew D.
Fontaine, Shaun D.
La Clair, James J.
DiPasquale, Antonio G.
Rheingold, Arnold L.
Burkart, Michael D.
CHEMICAL COMMUNICATIONS, 2006, (44) : 4602 - 4604

← 1 2 3 4 5 →