Regioselective oxidation of β-hydroxyazo compounds to β-hydroxyazoxy compounds and its application to syntheses of maniwamycins A and B

Nakata, Masaya; Kawazoe, Shohei; Tamai, Tetsuro; Tatsuta, Kuniaki; Ishiwata, Hiroyuki; Takahashi, Yoshio; Okuno, Yukihiro; Deushi, Takeo

doi:10.1016/s0040-4039(00)61737-9

Cited by 29 publications

(25 citation statements)

References 32 publications

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“…In cases of unsymmetrically substituted epoxides or hydrazines, regioisomeric hydrazinoalcohols can be formed, the ratio of which is influenced by the steric and electronic properties of the substituents [23][24][25][26][27][28][29]. Because of the difficulties arising from the tedious separation and/or correct identification of all the possible isomers, the ratios of the regioisomers formed are rarely mentioned in the publications.…”

Section: Epoxide Ring-openings With Hydrazine Derivatives (Methods A)mentioning

confidence: 99%

“…Removal of the Cbz groups was achieved by catalytic hydrogenation [26]. It is interesting to note that N 2 -methylsubstituted hydrazinoalcohol 36, prepared by the previous process, is the unfavorable regioisomeric product of the ringopening reaction of 1,2-epoxyhexane (17) with methylhydrazine.…”

Section: Nucleophilic Substitution Reactions By Using Hydrazines (Metmentioning

confidence: 99%

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Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Zalán

Lázár

Fülöp

2005

COC

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Hydrazinoalcohols are versatile di-or trifunctional compounds with wide-ranging possibilities for application in organic synthesis. Numerous methods have been devised for the preparation of this family of compounds in recent decades. This review discusses the main pathways for the synthesis of hydrazinoalcohol derivatives, including epoxide ring-openings and nucleophilic substitutions by hydrazines, addition reactions to hydroxyhydrazones, hydrazine additions to olefinic bonds, electrophilic C-and N-amination reactions, cycloadditions, reductions of N-nitroso aminoalcohols and some unique procedures. The latest developments in these fields, involving both conventional and enzymatic catalytic methods of synthetic organic chemistry, allow the highly regio-, stereo-and enantioselective preparation of hydrazinoalcohol derivatives.

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Section: Epoxide Ring-openings With Hydrazine Derivatives (Methods A)mentioning

confidence: 99%

Section: Nucleophilic Substitution Reactions By Using Hydrazines (Metmentioning

confidence: 99%

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Zalán

Lázár

Fülöp

2005

COC

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“…Meanwhile, total syntheses of both compounds have been achieved through regioselective oxidation of the azo precursor. 58,59 The maniwamycin congeners maniwamycins C−F (11−14) were discovered from the culture broth of Streptomyces sp. TOHO-M025.…”

Section: ■ Microbial Azoxy Compoundsmentioning

confidence: 99%

“…Although 9 and 10 were patented for potential use for mycosis treatment, no follow-up work on clinical trials has yet been done since the patent was submitted. Meanwhile, total syntheses of both compounds have been achieved through regioselective oxidation of the azo precursor. , …”

Section: Microbial Azoxy Compoundsmentioning

confidence: 99%

Chemistry and Biology of Natural Azoxy Compounds

Wibowo

Ding

2020

J. Nat. Prod.

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Azoxy compounds belong to a small yet intriguing group of natural products sharing a common functional group with the general structure RNN+(O–)R. Their intriguing chemical structures, diverse biological activities, and important industrial applications have received attention from researchers in natural product chemistry, total synthesis, and biosynthesis. This review presents current updates about the structural diversity of natural azoxy compounds isolated from different organisms and highlights the enzymes and biological logic involved in their construction. We assume that the identification of key enzymes will provide efficient tools in biocatalysis to generate new azoxy compounds, while genome mining may result in novel natural azoxy compounds of medical and industrial interest.

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“…[5][6][7][8][9] Most 1,2-disubstituted aliphatic hydrazines and azoalkanes are metabolized in humans via azoxy intermediates. 5 Since the discovery of macrozamin in 1951, [10][11][12][13][14] a number of naturally occurring azoxy compounds have been identified, including cycasin, 15,16 elaiomycin, 17 maniwamycin I, 18,19 azoxybacillin, …”

Section: Introductionmentioning

confidence: 99%

The free radical chemistry of the azoxy group

Engel¹,

Duan²,

Shu-Lin³

et al. 2003

Arkivoc

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The azoxy functional group, though relatively uncommon, is found in several natural products and in liquid crystalline compounds. Azoxyalkanes are generally very stable to heat and light and are not subject to attack by radicals. Intramolecular radical reactions, however, can lead to cyclic aminyl nitroxides and hydrazyls, which rearrange further or undergo fragmentation. The azoxy group greatly stabilizes an attached carbon-centered radical but the chemistry of the resulting α-azoxy radicals is not completely understood.

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Regioselective oxidation of β-hydroxyazo compounds to β-hydroxyazoxy compounds and its application to syntheses of maniwamycins A and B

Cited by 29 publications

References 32 publications

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Chemistry and Biology of Natural Azoxy Compounds

The free radical chemistry of the azoxy group

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