Synthesis of β-carbolines from aldehydes and ketones via the α-siloxy α,β-unsaturated esters

被引：8

作者：

He, Shuwen ^{[1
]}

Lai, Zhong ^{[1
]}

Yang, David X. ^{[1
]}

Hong, Qingmei ^{[1
]}

Reibarkh, Mikhail ^{[1
]}

Nargund, Ravi P. ^{[1
]}

Hagmann, William K. ^{[1
]}

机构：

[1] Merck Res Labs, Dept Med Chem, Rahway, NJ 07065 USA

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 33期

关键词：

beta-Carboline; Pictet-Spengler reaction; alpha-Siloxy alpha; beta-unsaturated ester; Tiyptamine; alpha-Ketoester; ACYL ANION EQUIVALENT; DERIVATIVES; EFFICIENT; ALKALOIDS;

D O I：

10.1016/j.tetlet.2010.06.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an efficient method for the synthesis of beta-carbohnes from alpha-siloxy alpha,beta-unsaturated esters, which are accessible from a variety of aldehydes and ketones. (c) 2010 Elsevier Ltd All rights reserved

引用

页码：4361 / 4364

页数：4

共 50 条

[1] New application of bromotrimethylsilane:: Elaboration of aldehydes/ketones into homologous α,β-unsaturated esters via β-hydroxy esters
Suri, SC
Marcischak, JC
[J]. SYNTHETIC COMMUNICATIONS, 2005, 35 (03) : 379 - 387
[2] Practical synthesis of (E)-α,β-unsaturated esters from aldehydes
List, B
Doehring, A
Fonseca, MTH
Wobser, K
van Thienen, H
Torres, RR
Galilea, PL
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) : 1558 - 1560
[3] PREPARATION OF CYCLOPROPANES FROM ALPHA, BETA-UNSATURATED ALDEHYDES, ESTERS, AND KETONES
CHANG, YH
PINNICK, HW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (02): : 373 - 374
[4] A Stereoselective and Practical Synthesis of (E)-α,β-Unsaturated Ketones from Aldehydes
Balducci, Evita
Attolino, Emanuele
Taddei, Maurizio
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (02) : 311 - 318
[5] Direct Synthesis of ,-Unsaturated -Keto Esters from Aldehydes and Pyruvates
Mansaray, John Kamanda
Sun, Jiarui
Huang, Shisheng
Yao, Weijun
[J]. SYNLETT, 2019, 30 (07) : 809 - 812
[6] SYNTHESIS OF ALDEHYDES BY A ONE CARBON HOMOLOGATION OF KETONES AND ALDEHYDES VIA ALPHA,BETA-UNSATURATED ISOCYANIDES
MOSKAL, J
VANLEUSEN, AM
[J]. RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1986, 105 (04): : 141 - 142
[7] VERSATILE SYNTHESIS OF ALPHA, BETA-UNSATURATED ALDEHYDES AND NITRILES FROM KETONES VIA VILSMEIER FORMYLATION
TRAAS, PC
TAKKEN, HJ
BOELENS, H
[J]. TETRAHEDRON LETTERS, 1977, (23) : 2027 - 2030
[8] Efficient Alkenation of Aldehydes and Ketones to α,β-Unsaturated Esters Using α,α-Bis(dimethylsilyl)-substituted Esters
Miura, Katsukiyo
Ebine, Masaru
Ootsuka, Kazunori
Ichikawa, Junji
Hosomi, Akira
[J]. CHEMISTRY LETTERS, 2009, 38 (08) : 832 - 833
[9] New odorless protocols for the synthesis of aldehydes and ketones from thiol esters
Miyazaki, T
Han-ya, Y
Tokuyama, H
Fukuyama, T
[J]. SYNLETT, 2004, (03) : 477 - 480
[10] Palladium-mediated synthesis of aldehydes and ketones from thiol esters
Fukuyama, T
Tokuyama, H
[J]. ALDRICHIMICA ACTA, 2004, 37 (03) : 87 - 96

← 1 2 3 4 5 →