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Synthetic Studies on Heterocyclic Antibiotics Containing Nitrogen Atoms

  • Hiromasa KiyotaEmail author
Chapter
Part of the Topics in Heterocyclic Chemistry book series (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).

Antibiotics Antimycins Glutarimides Tabtoxins Total synthesis 

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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Authors and Affiliations

  1. 1.Graduate School of Agricultural ScienceTohoku UniversityAoba-ku SendaiJapan

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