Improved method for the synthesis of (E)-cyclic-β-alkoxyacrylates under mild conditions

被引：46

作者：

Kato, K

Nishimura, A

Yamamoto, Y

Akita, H

机构：

[1] Toho Univ, Sch Pharmaceut Sci, Funabashi, Chiba 2748510, Japan

[2] Toho Univ, Fac Sci, Dept Chem, Funabashi, Chiba 2748510, Japan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 25期

关键词：

D O I：

10.1016/S0040-4039(01)00689-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxidative cyclization-methoxycarbonylation of cyclic- and acyclic-4-yn-l-ols 1 in the presence of Pd(II)ly-benzoquinone in methanol at 0 degreesC under a carbon monoxide atmosphere (balloon) afforded (E)-cyclic-beta -alkoxyacrylates 2 in good to excellent yields. The present reaction is applicable to the above-mentioned substrates bearing the additional functional groups such as acetate, hydroxyl, ketone, ester, terminal acetylene and the acid-sensitive protecting groups (TBDPS, TBDMS, MOM and THP). A new synthesis of the left part of the cystothiazoles is presented. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4203 / 4205

页数：3

共 16 条

[1]

ALI BE, 1991, J ORG CHEM, V56, P1099

[2] ANTIBIOTICS FROM BASIDIOMYCETES .18. STROBILURIN C AND OUDEMANSIN-B, 2 NEW ANTI-FUNGAL METABOLITES FROM XERULA SPECIES (AGARICALES) [J].