First Total Synthesis of Naturally Occurring (−)‐Nitidon and Its Enantiomer

Bellina, Fabio; Carpita, Adriano; Mannocci, Luca; Rossi, Renzo

doi:10.1002/ejoc.200400101

Cited by 59 publications

(33 citation statements)

References 53 publications

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“…In addition, mucohalic acids' high reactivity has been exploited for the preparation of stereodefined acyclic unsaturated dihalogenated derivatives and sulphur-or nitrogen-containing heterocycles including precursors of agrochemicals [10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of azido derivatives of mucobromic acid

Jumbam¹,

Masamba²,

Mbebe³

2012

Bull. Chem. Soc. Eth.

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ABSTRACT. Mucobromic acid is a highly reactive multicentered molecule. It was converted to its corresponding but unstable diazido derivative by reaction with two equivalents of sodium azide. The resultant 3,4-diazido-5-hydroxyfuran-2(5H)-one was obtained in moderate yield (42%) but decomposed readily even at low temperatures. Its more stable analogue 3,4-diazido-5-methoxyfuran-2(5H)-one was obtained in excellent yield after reacting 5-methoxy-3,4-dibromofuranone with two equivalents of sodium azide. The 4,5-dibromopyridazinones which are in effect masked mucobromic acid derivatives, underwent nucleophilic substitution reactions with various nucleophiles, including azides and afforded corresponding azidopyridazinones in good yields. The synthesized azido-furanone and pyridazinone derivatives are earmarked for click reactions.

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Section: Introductionmentioning

confidence: 99%

Synthesis of azido derivatives of mucobromic acid

Jumbam¹,

Masamba²,

Mbebe³

2012

Bull. Chem. Soc. Eth.

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“…2(5H) Furanone structural fragments are parts of natural biologically active compounds such as clavacin, penicillic acid, vitamin C, and synthetic pharmaceutical sub stances. [1][2][3][4] The interest in mucochloric acid from the standpoint of theoretical and experimental organic chemistry is due to its structural features (ring-chain tautomerism) and to the presence of a number of reaction centers owing to which this acid and its derivatives can be involved, as effective building blocks, in reactions with nucleophilic, electrophilic, and other reagents. 1 A large number of publications are devoted to reactions of 2(5H) furanones with N , С , О , and Р nucleophiles; however, among reactions with S nucleophiles, only those with thiols were described.…”

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confidence: 99%

Reactions of 2-mercaptoacetic acid with mucochloric acid and its derivatives

Kurbangalieva¹,

Devyatova²,

Kosolapova³

et al. 2009

Russ Chem Bull

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The stable products of reactions of mucochloric acid and some of its ethers with 2 mer captoacetic acid were synthesized and characterized. The variation of experimental conditions allowed targeted introduction of a sulfur containing fragment into particular position of the heterocycle: the reaction in aqueous potassium hydroxide gives 3 substituted 2(5H) furanone, the triethylamine additive in nonaqueous solvents facilitates the formation of 4 substituted products, and acid catalysis results in the replacement of the hydroxy (methoxy) group at С(5).(3,4 Dichloro 2 oxo 2,5 dihydrofuran 5 ylthio)ethanoic acid and (3 chloro 5 hydroxy 2 oxo 2,5 dihydrofuran 4 ylthio)ethanoic acid were characterized by X ray diffraction; their crystal and gas phase structures were discussed. The 5 monosubstituted product crystallizes as a racemate, while 4 monosubstituted product, as a conglomerate.

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confidence: 99%

“…α-Pyrone derivatives have also been used as synthetic intermediates in organic synthesis [28,29,[31][32][33][34].…”

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confidence: 99%

An expedient and green ultrasound-promoted synthesis of fused α-pyrones from Baylis–Hillman acetates using basic ionic liquid [bdmim]OH

Mamaghani

Alavi

2015

J IRAN CHEM SOC

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α-Pyrone derivatives have also been used as synthetic intermediates in organic synthesis [28,29,[31][32][33][34].Thus, several protocols for the synthesis of α-pyrones and related compounds by numerous approaches have been reported. Such as gold (I)-catalyzed reaction of terminal alkynes and propiolic acids [35], palladium catalyzes annulation of alkynes [36,37], K 2 CO 3 -catalyzed Michael addition-lactonization of 1,2-allenic ketones [38], palladium-catalyzed coupling of 3-halo-(2Z)-enoic acids, 3-halo-(2Z)-enoates with allenylstannanes [39,40], from Baylis-Hillman adducts [40][41][42][43] and several others [44][45][46][47][48][49][50][51][52][53][54][55][56][57][58]. Some of these methods, despite their elegance, have drawbacks such as use of toxic catalysts and solvents, low yielding of products, harsh reaction conditions, lack of regioselectivity and suffering from multi-step reaction. As a result, development of a simple and green protocol for the α-pyrones is highly required.On the other hand, one of the most important principles of the green chemistry is elimination of hazardous solvents in chemical synthesis and avoiding use of toxic catalysts. Ionic liquids have been widely used as greener solvents, suitable for a range of organic reactions [59] and providing possibilities such as control of product distribution, enhanced rate, ease of product recovery and immobilization of catalyst [60][61][62][63][64][65][66][67][68][69][70]. Basic ionic liquids have been increasingly used as environmentally friendly solvents and catalysts with high activity and selectivity and easily recovered materials instead of traditional bases such as KOH, NaOH, K 2 CO 3 , NaHCO 3 , NaOAc, triethylamine, or tetrabutylammonium acetate [71][72][73]. In addition, ultrasound irradiation as a green source of energy has also been utilized to accelerate organic reactions, leading to desired products in shorter reaction time, higher yield and milder condition [74][75][76][77][78].Abstract Fused α-pyrones were obtained in a convenient and green protocol from Baylis-Hillman acetates and various cyclic dicarbonyl compounds in the presence of basic ionic liquid 1-butyl-2,3-dimethylimidazolium hydroxide ([bdmim]OH) under ultrasonic irradiation. This method provided the desired α-pyrones in good to high yields (82-98 %) and lower reaction times (5-15 min).

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First Total Synthesis of Naturally Occurring (−)‐Nitidon and Its Enantiomer

Cited by 59 publications

References 53 publications

Synthesis of azido derivatives of mucobromic acid

Synthesis of azido derivatives of mucobromic acid

Reactions of 2-mercaptoacetic acid with mucochloric acid and its derivatives

An expedient and green ultrasound-promoted synthesis of fused α-pyrones from Baylis–Hillman acetates using basic ionic liquid [bdmim]OH

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