Regioselective ring-closing metathesis on terpenoid acrylates and acrylamides

被引：16

作者：

Du, YM ^{[1
]}

Wiemer, DF ^{[1
]}

机构：

[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 35期

关键词：

D O I：

10.1016/S0040-4039(01)01179-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of acrylate esters was prepared by treatment of representative terpenoid aldehydes with allyl or vinyl magnesium bromide followed by reaction with acryloyl chloride. In all cases, ring-closing metathesis (RCM) resulted in regioselective formation of unsaturated lactones through metathesis of the acrylate and terminal olefins. After condensation of farnesal with a primary amine, a parallel series of reactions led to Formation of the corresponding lactam. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：6069 / 6072

页数：4

相关论文

共 21 条

[1] A convenient method for the efficient removal of ruthenium byproducts generated during olefin metathesis reactions [J].

Ahn, YM ;

Yang, K ;

Georg, GI .

ORGANIC LETTERS, 2001, 3 (09) :1411-1413

[2]

Armstrong SK, 1998, J CHEM SOC PERK T 1, P371

[3] Synthesis of nonracemic dimethyl α-(hydroxyfarnesyl)phosphonates via oxidation of dimethyl farnesylphosphonate with (camphorsulfonyl)oxaziridines [J].

Cermak, DM ;

Du, YM ;

Wiemer, DF .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (02) :388-393

[4] 2-(acyloxy)ethylphosphonate analogues of prenyl pyrophosphates: Synthesis and biological characterization [J].

Cermak, DM ;

Wiemer, DF ;

Lewis, K ;

Hohl, RJ .

BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (12) :2729-2737

[5] CATALYTIC RING-CLOSING METATHESIS OF FUNCTIONALIZED DIENES BY A RUTHENIUM CARBENE COMPLEX [J].

FU, GC ;

NGUYEN, ST ;

GRUBBS, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9856-9857

[6]

Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012

[7] Ring-closing metathesis strategy to unsaturated γ- and δ-lactones:: Synthesis of hydroxyethylene isostere for protease inhibitors [J].

Ghosh, AK ;

Cappiello, J ;

Shin, D .

TETRAHEDRON LETTERS, 1998, 39 (26) :4651-4654

[8] RING-CLOSING METATHESIS AND RELATED PROCESSES IN ORGANIC-SYNTHESIS [J].

GRUBBS, RH ;

MILLER, SJ ;

FU, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (11) :446-452

[9] Ring closing metathesis reactions on a phosphonate template [J].

Hanson, PR ;

Stoianova, DS .

TETRAHEDRON LETTERS, 1998, 39 (23) :3939-3942

[10] Phosphonate and bisphosphonate analogues of farnesyl pyrophosphate as potential inhibitors of farnesyl protein transferase [J].

Holstein, SA ;

Cermak, DM ;

Wiemer, DF ;

Lewis, K ;

Hohl, RJ .

BIOORGANIC & MEDICINAL CHEMISTRY, 1998, 6 (06) :687-694