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Synthetic Studies on Heterocyclic Antibiotics Containing Nitrogen Atoms

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Bioactive Heterocycles I

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 6))

Abstract

A variety of heterocyclic antibiotics and phytotoxins have been found to date. Total and semi-synthesis of these natural products and related analogous compounds are essential for the elucidation of structure–activity relationships and the development of useful agrochemicals and medicines. Early and recent examples are described, including synthetic studies of glutarimide antibiotics (cycloheximide and related aliphatic and macrolactone derivatives), antimycins (antimycin A and related diolides), and tabtoxins (amino acids with a hydroxy β-lactam ring).

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Abbreviations

AA:

Antimycins A

aq.:

aqueous

DCM:

Dichloromethane

cat.:

Catalyst

CHX:

Cycloheximide

DEPC:

Diethylphosphoryl chloride

DHP:

3,4-Dihydro-2H-pyran

(DHQ)2PHAL:

1,4-Bis(9-O-dihydrochininyl)phthalazine

DIAD:

Diisopropyl azodicarboxylate

dil.:

Diluted

EDCI:

N-Ethyl-N′-(3′-dimethylaminopropyl)carbodiimide

DNB:

3,5-Dinitrobenzoyl

HOBt:

1-Hydroxybenzotriazole

MMPP:

Magnesium monoperoxyphthalate

MPM:

p-Methoxyphenylmethyl (PMB)

MS4A:

Molecular sieves 4 Å

NMM:

N-Methylmorpholine

oxi.:

Oxidation

quant.:

Quantitative

sat.:

Saturated

SAR:

Structure–activity relationships

TBS:

t-Butyldimethylsilyl

TβL:

Tabtoxinine-β-lactam

TEMPO:

2,2,6,6-Tetramethylpiperidinyloxy radical

TES:

Triethylsilyl

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  1. Graduate School of Agricultural Science, Tohoku University, 1-1 Tsutsumidori-Amamiyamachi, 981-8555, Aoba-ku Sendai, Japan

    Hiromasa Kiyota

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  1. Hiromasa Kiyota
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Correspondence to Hiromasa Kiyota .

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Shoji Eguchi

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Kiyota, H. Synthetic Studies on Heterocyclic Antibiotics Containing Nitrogen Atoms. In: Eguchi, S. (eds) Bioactive Heterocycles I. Topics in Heterocyclic Chemistry, vol 6. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_032

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