Total synthesis of tubastrine and 3-dehydroxy tubastrine by microwave-assisted cross-coupling reactions

被引：9

作者：

Lorentzen, Marianne ^{[1
]}

Bayer, Annette ^{[2
]}

Sydnes, Magne O. ^{[1
]}

Jorgensen, Kare B. ^{[1
]}

机构：

[1] Univ Stavanger, Fac Sci & Technol, Dept Math & Nat Sci, NO-4036 Stavanger, Norway

[2] Arctic Univ Norway, UiT, Fac Sci & Technol, Dept Chem, NO-9037 Tromso, Norway

来源：

TETRAHEDRON | 2015年 / 71卷 / 43期

关键词：

Natural product synthesis; C-N cross-coupling; Hunsdiecker-Borodin reaction; Tubastrine; Microwave-assisted reaction; EFFICIENT SYNTHESIS; VINYL HALIDES; HECK REACTION; IONIC LIQUID; ACID; ARYL; GUANIDINYLATION; INHIBITORS; ALKALOIDS; ENAMIDES;

D O I：

10.1016/j.tet.2015.09.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first syntheses of tubastrine and 3-dehydroxy tubastrine are described. The target compounds were prepared in four consecutive steps from commercially available starting materials. The central scaffold was formed by a microwave-assisted C-N cross-coupling reaction between 1,3-bis(tert-butoxycarbonyl)-guanidine and (E)-((4-(2-iodovinyl)-1,2-phenylene)bis(oxy))bis(tert-butyldimethylsilane) and (E)-tertbutyl(4-(2-iodovinyl)phenoxy)-dimethylsilane, respectively. The aryl vinyl iodides were obtained by a Hunsdiecker-Borodin-type reaction of aryl acrylic acids, which were easily available from trans-caffeic acid or trans-p-coumaric acid. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：8278 / 8284

页数：7

共 50 条

[21] Copper-catalyzed coupling of amides and carbamates with vinyl halides [J].

Jiang, L ;

Job, GE ;

Klapars, A ;

Buchwald, SL .

ORGANIC LETTERS, 2003, 5 (20) :3667-3669

[22] QUANTITATIVE DEALKYLATION OF ALKYL ETHERS VIA TREATMENT WITH TRIMETHYLSILYL IODIDE - NEW METHOD FOR ETHER HYDROLYSIS [J].

JUNG, ME ;

LYSTER, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (23) :3761-3764

[23]

Kuang CX, 2000, SYNLETT, P1439

[24] Microwave-promoted palladium-catalyzed coupling reactions [J].

Larhed, M ;

Hallberg, A .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9582-9584

[25] A NEW SYNTHESIS OF SUBSTITUTED FULVENES [J].

LEE, GCM ;

TOBIAS, B ;

HOLMES, JM ;

HARCOURT, DA ;

GARST, ME .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (25) :9330-9336

[26] Novel aminopeptidase N inhibitors derived from antineoplaston AS2-5 (Part II) [J].

Li, Xun ;

Wang, Yazhou ;

Wu, Jifeng ;

Li, Yonggang ;

Wang, Qiang ;

Xu, Wenfang .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (08) :3061-3071

[27] Sequential copper-catalyzed vinylation/cyclization: An efficient synthesis of functionalized oxazoles [J].

Martin, Rubn ;

Cuenca, Ana ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2007, 9 (26) :5521-5524

[28] Microwave-assisted solvent-free synthesis of trans-cinnamic acids using lithium chloride as catalyst [J].

Mogilaiah, K ;

Reddy, GR .

SYNTHETIC COMMUNICATIONS, 2004, 34 (02) :205-210

[29] Solid-phase oxidative halodecarboxylation of β-arylacrylic acids with the ceric ammonium nitrate-alkali halide system [J].

Nikishin, G. I. ;

Sokova, L. L. ;

Makhaev, V. D. ;

Kapustina, N. I. .

RUSSIAN CHEMICAL BULLETIN, 2008, 57 (01) :118-123

[30] Rapid synthesis of the tetrahydroquinoline alkaloids: angustureine, cuspareine and galipinine [J].

O'Byrne, Aisling ;

Evans, Paul .

TETRAHEDRON, 2008, 64 (35) :8067-8072

← 1 2 3 4 5 →