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

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