Hydroxyl Substitution Studies at the 5″‐Position in the Neomycin B Series: Introduction of a Phtalimide Group Under Mitsunobu Reaction Conditions

Linares, Angélica Hernández; Fourmy, Dominique; Fourrey, Jean‐Louis; Loukaci, Ali

doi:10.1080/00397910500384921

Cited by 6 publications

(4 citation statements)

References 15 publications

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“…The inversion process (>99% ee ) in this reaction was corroborated by a combination of NMR spectroscopy and molecular modeling. Linares et al reported that although the phthalimido group could be readily introduced at the 5′′-position of ribostamycin, a similar reaction was not possible on neomycin B, wherein a competitive bicyclization process involving other functional groups occurred . Deguin and co-workers were able to introduce more than one NH 2 group using a phthalimide protocol in the conversion of aucubin into aminoside antibiotic analogues, diamino-dideoxyaucubin and triamino-trideoxyaucubin .…”

Section: Amines Amides (Including Nucleobases) or Azides As Nucleophilesmentioning

confidence: 99%

“…Linares et al reported that although the phthalimido group could be readily introduced at the 5′′-position of ribostamycin, a similar reaction was not possible on neomycin B, wherein a competitive bicyclization process involving other functional groups occurred. 805 Deguin and co-workers were able to introduce more than one NH 2 group using a phthalimide protocol in the conversion of aucubin into aminoside antibiotic analogues, diamino-dideoxyaucubin and triamino-trideoxyaucubin. 806 They had earlier prepared polyfunctionalized tetrahydro-1H-cyclopenta[c]furan glucosides also by starting with aucubin.…”

Section: N-alkylation Using Phthalimide and Related Imidesmentioning

confidence: 99%

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Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

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His research interests include Organophosphorus Chemistry and Main Group Chemistry. He has over 115 publications so far and is a fellow of the Indian Academy of Sciences, Bangalore. N. N. Bhuvan Kumar was born in Cherukupalli, Guntur, India. After completing his B.Sc. from Nagarjuna University, he joined the School of Chemistry, University of Hyderabad, as a postgraduate student in the year 2000 and obtained his Master's degree in Chemistry. Currently, he is pursuing a Ph.D. on Organophosphonates under the supervision of Prof. K. C. Kumara Swamy. E. Balaraman was born in Kancheepuram, Chennai, India, in 1980. He received his M.Sc. in Chemistry from Vivekananda College [Madras University (2002)] and his Ph.D. degree in the areas of organophosphonates and modified BINOLs under the guidance of Prof. K. C. Kumara Swamy. Presently he is a postdoctoral fellow with Professors David Milstein and Ronny Neumann at the Weizmann Institute of Science, Israel. K. V. P. Pavan Kumar was born in Hyderabad (Andhra Pradesh), India, in 1979. He obtained his B.Sc. (Chemistry Honors) and M.Sc. (Chemistry) degrees from Sri Sathya Sai Institute of Higher Learning, Puttaparthi, A.P., India. He obtained his Ph.D. degree under the guidance of Prof. K. C. Kumara Swamy in October 2006. Presently he is working as a postdoctoral fellow in the area of hydroamination reactions using new titanium catalysts with Prof. Pierre Le Gendre at the Universite ´de Bourgogne, France.

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Section: Amines Amides (Including Nucleobases) or Azides As Nucleophilesmentioning

confidence: 99%

Section: N-alkylation Using Phthalimide and Related Imidesmentioning

confidence: 99%

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

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“…Apart from the bisanhydrido derivative 22 a monoanhydrido derivative, containing an oxirane ring and not containing an aziridine ring, was isolated with a yield of 33% (not shown in the scheme). Earlier compound 22, obtained under analogous conditions, was erroneously assigned a structure containing aziridine and azetidine rings [32].…”

Section: The Production Of Three-membered Ringsmentioning

confidence: 98%

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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“…As an approach to obtain the potential 5″-amino-5″deoxyneomycin 57, Linares and coworkers 42 used Mitsunobu reaction of N-Boc neomycin derivative 12 with diisopropylazodicarboxylate (DIAD) and triphenylphosphine in the presence of phthalimide to introduce the phthalimide group at the C-5″ position but a competitive bicyclization process occurred generating 57 within ring IV (Scheme 19) due to the reactivity of the idose moiety of the molecule (ring IV).…”

Section: Synthetic Modification Of Neomycin B (Neob)mentioning

confidence: 99%