Synthesis of novel bicyclic 2-amino-4(1h)-pyridones. Reaction of lactim ethers with α-cyanoacetone dianion.

Jiang, Jack B.; Urbanski, Maud

doi:10.1016/s0040-4039(01)80791-7

Cited by 12 publications

(4 citation statements)

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“…The plan was to prepare a key intermediate 8 having the A/B/D-rings of the natural product and then reduce the cyanoenamine moiety to set the C9,C10 stereochemistry and establish the attendant C11 hydroxymethyl group, ultimately leading to myrioneurinol. Compound 8 would be produced by cyclization of the anion of nitrile 9 onto an appropriate lactam imidate derivative to produce the B-ring of the alkaloid . Intermediate 9 would in turn be accessed by alkylation at C7 of the enolate of spirocyclic ester 10 followed by reduction of the C18 carboxylate to the corresponding hydroxymethyl group.…”

Section: Resultsmentioning

confidence: 99%

Construction of the Myrioneuron Alkaloids: A Total Synthesis of (±)-Myrioneurinol

2014

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A strategy has been developed that culminated in a stereoselective total synthesis of the tetracyclic antimalarial Myrioneuron alkaloid myrioneurinol. The synthesis relies on three highly diastereoselective reactions, including an intramolecular chelation-controlled Michael spirocyclization of an N-Cbz-lactam titanium enolate to an α,β-unsaturated ester for construction of the A/D-ring system and the attendant C5 (quaternary), C6 relative stereochemistry; a malonate enolate conjugate addition to a nitrosoalkene in order to install the appropriate functionality and establish the configuration at C7; and an intramolecular aza-Sakurai reaction to form the B-ring and the accompanying C9 and C10 stereocenters.

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Section: Resultsmentioning

confidence: 99%

Construction of the Myrioneuron Alkaloids: A Total Synthesis of (±)-Myrioneurinol

2014

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“…According to the authors of [71], the process leading to the formation of compounds 62 from the lactim ethers and the dianion of CH 2 COCHCN, produced in situ as a result of treatment of 5-methylisoxazole with (i-Pr) 2 NLi, takes place through the formation of the anion 63.…”

Section: °Cmentioning

confidence: 99%

“…The reaction does not go in the absence of methyl alcohol, since during the transformation of the anion 63 into the nitrile 64 proton exchange occurs as an essential stage for the subsequent addition of the nitrogen of the imino group to the CN group [71]. The reactions of lactim ethers with malonic esters have been studied in a number of papers [57,72,73].…”

Section: °Cmentioning

confidence: 99%

Five-, Six-, and Seven-membered Lactim Ethers. Methods of Synthesis and Chemical Properties. (Review)

Shvekhgeimer

2005

Chem Heterocycl Compd

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“…186 The dianion 241, generated on treatment of 5-methylisoxazole with LDA in THF, reacts with the imidate 6a giving rise to 2-amino-1-azabicyclo[4.4.0]deca-2,5-dien-4-one 242 (yield 40%). 187…”

Section: Reactions With Nitrilesmentioning

confidence: 99%

2,3,4,5-Tetrahydropyridine (Δ¹-piperideine) and its derivatives. Synthesis and chemical properties

Shvekhgeimer¹

1998

Russ. Chem. Rev.

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We study the influence of the tetragonalization occurring during the martensitic phase transition on the exchange interactions in Ni 2 MnGa Heusler alloy using first-principles calculations in conjunction with the frozen-magnon approximation. We show that the tetragonalization alters only the exchange constants characterizing the Mn-Mn interactions. Calculated Curie temperatures within the random-phase approximation are found to agree with experimental data. Moreover, we study the temperature dependence of the magnetization and the small deviation from the experimental data exactly at the temperature of the phase transition is discussed. Obtained results agree with previous theoretical results using Liechtenstein's formula to calculate the exchange constants and the Monte Carlo simulation technique to estimate the Curie temperature.have studied the exchange constants for the stoichiometric Ni 2 MnGa alloys for three values of the c/a ratio (c/a = 0.95, 1 and 1.25) using Liechtenstein's formula [31,32] while Monte Carlo simulations have been employed to estimate a Curie temperature of 375 K for the cubic austenitic phase [33]. Recently, the same group of authors have studied the exchange constants for the off-stoichiometric alloys both in the austenitic and martensitic phases [34,35], while Ghosh and Sanyal have focused only in the austenitic phase [36].

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Synthesis of novel bicyclic 2-amino-4(1h)-pyridones. Reaction of lactim ethers with α-cyanoacetone dianion.

Cited by 12 publications

References 11 publications

Construction of the Myrioneuron Alkaloids: A Total Synthesis of (±)-Myrioneurinol

Construction of the Myrioneuron Alkaloids: A Total Synthesis of (±)-Myrioneurinol

Five-, Six-, and Seven-membered Lactim Ethers. Methods of Synthesis and Chemical Properties. (Review)

2,3,4,5-Tetrahydropyridine (Δ¹-piperideine) and its derivatives. Synthesis and chemical properties

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Synthesis of novel bicyclic 2-amino-4(1h)-pyridones. Reaction of lactim ethers with α-cyanoacetone dianion.

Cited by 12 publications

References 11 publications

Construction of the Myrioneuron Alkaloids: A Total Synthesis of (±)-Myrioneurinol

Construction of the Myrioneuron Alkaloids: A Total Synthesis of (±)-Myrioneurinol

Five-, Six-, and Seven-membered Lactim Ethers. Methods of Synthesis and Chemical Properties. (Review)

2,3,4,5-Tetrahydropyridine (Δ1-piperideine) and its derivatives. Synthesis and chemical properties

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2,3,4,5-Tetrahydropyridine (Δ¹-piperideine) and its derivatives. Synthesis and chemical properties