A general strategy for the synthesis of azapeptidomimetic lactams

Broadrup, Robert L.; Wang, Bei; Malachowski, William P.

doi:10.1016/j.tet.2005.08.029

Cited by 23 publications

(16 citation statements)

References 49 publications

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“…The cyclization of the hydrazide 43 takes place readily with the formation of a five-membered ring [39]. …”

Section: The Production Of Five-membered Ringsmentioning

confidence: 99%

“…Cyclizations of hydroxamates, hydrazides, and sulfonamides containing a hydroxy group at a suitable position under Mitsunobu reaction conditions have been widely used in the synthesis of piperidine alkaloids and their analogs (Table 8) [30, 39,48,[59][60][61][62]. An intramolecular Mitsunobu reaction leading to the formation of a piperidine ring with the participation of an alkoxyamino group is also known ( Table 8, No.…”

Section: The Production Of Six-membered Ringsmentioning

confidence: 99%

“…In this case a considerable excess of PPh 3 and DEAD is required for more complete conversion. A series of peptidomimetics containing a β-lactam fragment, potential new protease inhibitors, was obtained by cyclization of the hydrazides 31 -derivatives of serine and threonine (Table 4) [38,39].…”

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confidence: 99%

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The Mitsunobu reaction in the chemistry of nitrogen-containing heterocyclic compounds. The formation of heterocyclic systems (review)

Голанцов

Карчава

Yurovskaya

2008

Chem Heterocycl Comp

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Methods for the design of nitrogen-containing heterocyclic systems involving the formation of C-N bonds under the conditions of the Mitsunobu reaction are discussed.The Mitsunobu reaction [1][2][3][4] is the reaction of compounds containing a mobile hydrogen atom HX with alcohols in the presence of a reagent system consisting of an azodicarboxylic ester and a phosphine PR 1 3 . This reaction results in the formation of an alkylation product RX accompanied by oxidation of the phosphine PR 1 3 to phosphine oxide R 1 3 P=O and reduction of the azodicarboxylic ester to the corresponding hydrazine.The reaction takes place under very mild conditions and usually at room temperature. If a chiral secondary alcohol ROH is used, the reaction is usually stereospecific and is accompanied by inversion of the configuration at the asymmetric carbon atom of the alcohol [1-3].From the moment of the first report [5] the Mitsunobu reaction became a powerful tool in synthetic organic chemistry and found widespread use in the synthesis of various heterocyclic compounds, optically active substances, steroids, alkaloids, carbohydrates, and nucleosides [1][2][3][4]6]. In particular, in a number of cases the Mitsunobu reaction has made it possible to synthesize new physiologically active compounds or to put forward new highly effective approaches to synthesis. Several reviews have been devoted to the Mitsunobu reaction [1-4, 6, 7]. Data on the use of the Mitsunobu reaction in the synthesis of alkaloids were reviewed in [6]. Various experimental techniques that make it possible to simplify the isolation of the products of the Mitsunobu reaction RX from the reaction mixture, including the use of reagents attached to a polymer support, were discussed in [7]. _______ * Dedicated to Afanasi Andreevich Akhrem on his 95th birthday. _________________________________________________________________________________________

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“…The cyclization of the hydrazide 43 takes place readily with the formation of a five-membered ring [39]. …”

Section: The Production Of Five-membered Ringsmentioning

confidence: 99%

Section: The Production Of Six-membered Ringsmentioning

confidence: 99%

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The Mitsunobu reaction in the chemistry of nitrogen-containing heterocyclic compounds. The formation of heterocyclic systems (review)

Голанцов

Карчава

Yurovskaya

2008

Chem Heterocycl Comp

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“… 14 Furthermore, the approach avoided the use of methylamine in a high pressure reaction vessel, which was required for conversion of the tosylate into 4 . 15 The amine 4 was reacted with the mesylate 6 , prepared from the corresponding aspartic acid derivative, 16 to give 5 . Deprotection gave aza-SAM, 2 , in 44% yield ( Scheme 1 ).…”

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confidence: 99%

Identification of stable S-adenosylmethionine (SAM) analogues derivatised with bioorthogonal tags: effect of ligands on the affinity of the E. colimethionine repressor, MetJ, for its operator DNA

Joce¹,

Caryl²,

Stockley³

et al. 2009

Org. Biomol. Chem.

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“…Starting from N-Boc-and Obenzyl-protected L-aspartic acid 4, the g-carboxylic acid was reduced directly via the mixed anhydride formed with isobutyl chloroformate. 18 This step was carried out on a multigram scale to give 5 reproducibly in quantitative yield and further purification was not required. The resulting alcohol 5 was then subjected to a standard mesylation reaction using mesylchloride and triethylamine to give mesylate 6.…”

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confidence: 99%

A Concise Route to l-Azidoamino Acids: l-Azidoalanine, l-Azidohomoalanine and l-Azidonorvaline

Roth¹,

Thomas²

2009

Synlett

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A general strategy for the synthesis of azapeptidomimetic lactams

Cited by 23 publications

References 49 publications

The Mitsunobu reaction in the chemistry of nitrogen-containing heterocyclic compounds. The formation of heterocyclic systems (review)

The Mitsunobu reaction in the chemistry of nitrogen-containing heterocyclic compounds. The formation of heterocyclic systems (review)

Identification of stable S-adenosylmethionine (SAM) analogues derivatised with bioorthogonal tags: effect of ligands on the affinity of the E. colimethionine repressor, MetJ, for its operator DNA

A Concise Route to l-Azidoamino Acids: l-Azidoalanine, l-Azidohomoalanine and l-Azidonorvaline

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A general strategy for the synthesis of azapeptidomimetic lactams

Cited by 23 publications

References 49 publications

The Mitsunobu reaction in the chemistry of nitrogen-containing heterocyclic compounds. The formation of heterocyclic systems (review)

The Mitsunobu reaction in the chemistry of nitrogen-containing heterocyclic compounds. The formation of heterocyclic systems (review)

Identification of stable S-adenosylmethionine (SAM) analogues derivatised with bioorthogonal tags: effect of ligands on the affinity of the E. colimethionine repressor, MetJ, for its operator DNA

A Concise Route to l-Azidoamino Acids: l-Azidoalanine, l-Azidohomo­alanine and l-Azidonorvaline

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A Concise Route to l-Azidoamino Acids: l-Azidoalanine, l-Azidohomoalanine and l-Azidonorvaline