Cerium(IV)-Catalyzed Deprotection of Acetals and Ketals under Mildly Basic Conditions

Markó, István E.; Ateş, Ali; Gautier, Arnaud; Leroy, B.; Plancher, Jean‐Marc; Quesnel, Yannick; Vanherck, Jean‐Christophe

doi:10.1002/(sici)1521-3773(19991102)38:21<3207::aid-anie3207>3.0.co;2-i

Cited by 98 publications

(48 citation statements)

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“…As a complementary study, and to test the 1,2,4-trioxane unit as a dual protecting group, liberating the 1,2-diol together with the corresponding carbonyl group, 18 2 was treated with low valent tin chloride 19 and Ce(IV) salts, 20 recently exploited for the deprotection of acetals. The expected deprotection did not occur.…”

Section: Methodsmentioning

confidence: 99%

Chemistry of 1,2,4-Trioxanes: Metal-Induced Deoxygenation and Rearrangement of the 1,2,4-Trioxane Obtained by Photooxidation of β-Ionone

Mischne¹

2002

Synthesis

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D e o x y g e n a t i o n a n d R e a r r a n g e m e n t o f t h e 1 , 2 , 4 -T r i o x a n e O b t a i n e d b y P h o t o o x i d a t i o n o f b-IononeAbstract: The reactivity of 2,2,6,8-tetramethyltricyclo(6.2.2.0 1,6 )dodecene (2) toward different metal salts has been explored. In the presence of Fe(II), Sn(II) and Ce(IV) ions, compound 2 underwent a rearrangement process to afford acyclic triketones Z-3 and E-3. The action of Zn powder in acetic acid resulted in an unexpected formation of furan 4 in high yield.

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Section: Methodsmentioning

confidence: 99%

Chemistry of 1,2,4-Trioxanes: Metal-Induced Deoxygenation and Rearrangement of the 1,2,4-Trioxane Obtained by Photooxidation of β-Ionone

Mischne¹

2002

Synthesis

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“…Treatment with montmorillonite K-10 under the same conditions previously used in our group for the hydrolysis of structurally similar ketals resulted in no deprotection. The use of p-toluenesulfonic acid in acetone or cerium ammonium nitrate in an acetonitrile/water mixture 17,18 did not yield the desired ketone 13 either.…”

Section: (-)-Dihydromenisdaurilide and (+)-Dihydroaquilegiolidementioning

confidence: 99%

Synthesis of (+)- and (-)-dihydromenisdaurilide and (+)- and (-)-dihydroaquilegiolide

Alibés¹,

Cantó²,

March³

et al. 2006

Arkivoc

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The natural products (-)-dihydromenisdaurilide, (-)-3, and (+)-dihydroaquilegiolide, (+)-4, were isolated in 1993, but synthetic reports related to these compounds are quite scarce. Only a synthesis of both natural isomers in enantioenriched form and a synthesis in enantiopure form of unnatural 3 and natural 4 have been reported. Starting from an enantiopure monoketal of pbenzoquinone, we have investigated several synthetic approaches to both lactones in enantiomerically pure form, but each of them resulted in racemization. Finally, partial hydrogenation of (+)-and (-)-menisdaurilide allowed the preparation of (+)-and (-)-dihydromenisdaurilide, respectively, and a Mitsunobu reaction applied to 3 afforded (+)-and (-)-dihydroaquilegiolide.

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“…Besides being a one-electron oxidizing agent, CAN also acts as either a Bronsted acid or a Lewis acid. [30][31][32] CAN is widely used in the oxidation of alcohols, 33 cleavage of acetals and ketals, 34 and formation of carbon-carbon 35,36 or carbon-heteroatom bonds, 36,37 including etherification, 38 esterification, 39 1,3-oxathioacetalisation, 40 etc. This paper reports the formation of cyclic acetal derivatives (3-8) of 1, instead of simple ethers, when reacted with various primary alcohols in the presence of CAN.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of anticancer activity of novel andrographolide derivatives

et al. 2015

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A series of 3,19-O-acetal derivatives of andrographolide (1) have been synthesized by protecting the hydroxyls at C-3 and C-19 through a novel route. All the derivatives were evaluated for in vitro anticancer activity. Among the synthesized derivatives, compounds 3, 3a, 3d, 3e, 7 and 8 showed potential cytotoxicity against human cancer cell lines A549 (lung), HeLa (cervical), ACHN (renal), B-16 (melanoma) and IEC-6 (small intestine). The binding mode conformation was evaluated through docking simulations, while bioavailability/drug-likeness was evaluated through predictive ADME screening studies. All the derivatives were characterized by spectroscopy and the stereochemistry of compounds 3a and 3e was also confirmed by X-ray analysis.

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Cerium(IV)-Catalyzed Deprotection of Acetals and Ketals under Mildly Basic Conditions

Cited by 98 publications

References 1 publication

Chemistry of 1,2,4-Trioxanes: Metal-Induced Deoxygenation and Rearrangement of the 1,2,4-Trioxane Obtained by Photooxidation of β-Ionone

Chemistry of 1,2,4-Trioxanes: Metal-Induced Deoxygenation and Rearrangement of the 1,2,4-Trioxane Obtained by Photooxidation of β-Ionone

Synthesis of (+)- and (-)-dihydromenisdaurilide and (+)- and (-)-dihydroaquilegiolide

Synthesis and evaluation of anticancer activity of novel andrographolide derivatives

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