Stereochemical control in the intramolecular Diels-Alder reaction. 2. Structural and electronic effects on reactivity and selectivity

Boeckman, Robert K.; Ko, Soo S.

doi:10.1021/ja00368a020

Cited by 98 publications

(31 citation statements)

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“…1,3-Dibromide 2 l was obtained by reaction of the corresponding dichloride 2 k [46] with NaBr in acetone under standard conditions and 2 m was obtained by radical allylic halogenation of 2-methyl-1-phenylprop-1-ene (Fluka) under standard protocol. [47] Finally, 1,3-dibromide 2 c, [48] 1,3-dimesylate 2 d, [49] 1,4-dibromides 2 g, o ± q, [50±52] and diodide 2 i [53] were prepared as previously described. Commercially available anhydrous analytical grade acetone (SDS) was used for the condensations while anhydrous MeOH, toluene, and THF were obtained by distillation from magnesium and sodium/ benzophenone under argon, respectively.…”

Section: Methodssupporting

confidence: 44%

C−C versus C−O Anionic Domino Cycloalkylation of Stabilized Carbanions: Facile One-Pot Stereoselective Preparation of Functionalized Bridged Bicycloalkanones and Cyclic Enol Ethers

et al. 2001

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alpha,alpha'-Diactivated cyclic- or acyclic ketones undergo a chemoselective base promoted (K2CO3, DBU) one-pot C-C cycloalkylation, with 1,3- and 1,4-dihalides having a cis-like fixed configuration. This reaction gives highly functionalized bicyclo[3.2.1]octan-9-one and bicyclo[4.2.1]nonan-9-one derivatives, which are easily transformed to seven- and eight-membered rings through a high yield retro-Dieckmann cleavage. Starting from trans-1,4-dibromo-2-butenes, the transformation is governed by stereoelectronic factors and leads, through a chemo- and stereoselective C-O cycloalkylation, to synthetically valuable monocyclic or fused polycyclic functionalized enol ethers of high synthetic value. Semiempirical calculations showed a small difference in energy and the late character of the transition states leading to cis and trans isomers of the corresponding fused polycyclic enol ethers. These results, although minimizing the influence of a destabilizing 1,3-interaction on the outcome of the reaction, are qualitatively in agreement with the experimental results.

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Section: Methodssupporting

confidence: 44%

C−C versus C−O Anionic Domino Cycloalkylation of Stabilized Carbanions: Facile One-Pot Stereoselective Preparation of Functionalized Bridged Bicycloalkanones and Cyclic Enol Ethers

et al. 2001

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“…Although a great deal is known about this reaction, there is still much that remains a mystery, particularly the subtle effects of sidechain substituents (5). In order to use these cycloadditions synthetically one must be able to predict the feasibility of the cyclization with various substitution patterns in both the reacting units themselves and the connecting chain.…”

Section: Introductionsupporting

confidence: 40%

The synthesis of trisubstituted cyclopentadienes and their reactivity in the intramolecular Diels–Alder reaction

Alward¹,

Fallis²

1984

Can. J. Chem.

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“…Azide derivative 5h was prepared by a sodium azide substitution of 10 , obtained from staring material 8 from the reported procedures. 57, 58 …”

Section: Chemistrymentioning

confidence: 99%

Triazole–Dithiocarbamate Based Selective Lysine Specific Demethylase 1 (LSD1) Inactivators Inhibit Gastric Cancer Cell Growth, Invasion, and Migration

et al. 2013

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Lysine specific demethylase 1 (LSD1), the first identified histone demethylase, plays an important role in epigenetic regulation of gene activation and repression. The up-regulated LSD1's expression has been reported in several malignant tumors. In the current study, we designed and synthesized five series of 1, 2, 3-triazole-dithiocarbamate hybrids and screened their inhibitory activity toward LSD1. We found that some of these compounds, especially compound 26, exhibited the most specific and robust inhibition of LSD1. Interestingly, compound 26 also showed potent and selective cytotoxicity against LSD1 overexpressing gastric cancer cell lines MGC-803 and HGC-27, as well as marked inhibition of cell migration and invasion, compared to 2-PCPA. Furthermore, compound 26 effectively reduced the tumor growth bared by human gastric cancer cells in vivo with no signs of adverse side effects. These findings suggested that compound 26 deserves further investigation as a lead compound in the treatment of LSD1 overexpressing gastric cancer.

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Stereochemical control in the intramolecular Diels-Alder reaction. 2. Structural and electronic effects on reactivity and selectivity

Cited by 98 publications

References 0 publications

C−C versus C−O Anionic Domino Cycloalkylation of Stabilized Carbanions: Facile One-Pot Stereoselective Preparation of Functionalized Bridged Bicycloalkanones and Cyclic Enol Ethers

C−C versus C−O Anionic Domino Cycloalkylation of Stabilized Carbanions: Facile One-Pot Stereoselective Preparation of Functionalized Bridged Bicycloalkanones and Cyclic Enol Ethers

The synthesis of trisubstituted cyclopentadienes and their reactivity in the intramolecular Diels–Alder reaction

Triazole–Dithiocarbamate Based Selective Lysine Specific Demethylase 1 (LSD1) Inactivators Inhibit Gastric Cancer Cell Growth, Invasion, and Migration

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