Aldol condensation versus conjugate addition:: Intramolecular cyclization using a combination of Lewis acid and 1,2-diol

被引：0

作者：

Yamada, S ^{[1
]}

Suemune, H ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch Pharmaceut Sci, Fukuoka 8128582, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2000年 / 48卷 / 08期

关键词：

decalin skeleton; Lewis acid; 1,2-diol; intramolecular 1,4-addition;

D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The reactivity of 3-substituted 4-methyl-4-(3-oxobutyl)-2-cyclohexen-1-ones (1) in the presence of a combination of a Lewis acid and a 1,2-diol was studied. The results suggest several factors that influence 6-membered ring formation, including two types of intramolecular aldol reaction and intramolecular 1,4-addition, due to the C3-substituent, Lewis acid, and the presence of diol, In this study, never methodology to prepare two types of decalin skeleton could be developed.

引用

页码：1171 / 1175

页数：5

共 15 条

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[3] Tandem Michael addition and intramolecular aldol cyclization of 1,2-dideoxy-1-nitroheptitols derived from sugars
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TETRAHEDRON LETTERS, 2005, 46 (21) : 3673 - 3676
[4] ACTIVATION OF CARBONYL FUNCTION BY 1,2-DIOL - NOVEL ASYMMETRIC SPIROCYCLIZATION BASED ON ACID-CATALYZED CONJUGATE ADDITION (DEC PG 1858, 1993)
SUEMUNE, H
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Wachter, Nanette M.
NMR SPECTROSCOPY IN THE UNDERGRADUATE CURRICULUM, 2013, 1128 : 91 - 102
[6] SYNTHETIC STUDIES ON 8-DEOXYSERRATININE TYPE ALKALOIDS - SELECTIVE CYCLIZATION OF THE 1,2-CYCLOHEXANEDIACETALDEHYDE DERIVATIVE BY INTRAMOLECULAR ALDOL CONDENSATION
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[7] Deracemization of 1,2-diol monotosylate derivatives by a combination of enzymatic hydrolysis with the Mitsunobu inversion using polymer-bound triphenylphosphine
Shimada, Yasutaka
Usuda, Kazumasa
Okabe, Hirokazu
Suzuki, Tsuguru
Matsumoto, Kazutsugu
TETRAHEDRON-ASYMMETRY, 2009, 20 (24) : 2802 - 2808
[8] A CONCISE SYNTHESIS OF (-)-DIHYDROPROTOLICHESTERINIC ACID VIA CONSECUTIVE STEREOCONTROLLED 1,4-CONJUGATE ADDITION AND SYN-ALDOL CONDENSATION-REACTIONS
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TETRAHEDRON LETTERS, 1995, 36 (20) : 3567 - 3570
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Tanaka, M
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TETRAHEDRON, 2004, 60 (10) : 2271 - 2281
[10] One-pot Synthesis of Indolino[2′,3′:1,2][60]fullerenes from Fullerene Epoxide: Lewis Acid-assisted Nucleophilic Addition Followed by Intramolecular Cyclization
Numata, Youhei
Kawashima, Jun-ichi
Hara, Takumi
Tajima, Yusuke
CHEMISTRY LETTERS, 2008, 37 (10) : 1018 - 1019

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