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Natural Product Synthesis I pp 43–72Cite as

Paraconic Acids—The Natural Products from Lichen Symbiont

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Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 243))

Abstract

Paraconic acids, belonging to the class of γ-butyrolactone natural products, display a broad range of biological activities such as antibiotic and antitumor properties. Consequently a great number of synthetic strategies have been devised for them, ranging from diastereoselective and chiral pool approaches to the application of asymmetric catalysis. This review gives a critical account on the different methods developed that lead to paraconic acids of great structural variety.

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Abbreviations

Ac:

Acetyl

AIBN:

2,2′-Azobisisobutyronitrile

9-BBN:

9-Borabicyclo[3.3.1]nonane

Bn:

Benzyl

Bu:

Butyl

t-Bu:

tert-Butyl

Bz:

Benzoyl

CAN:

Ceric ammonium nitrate

cat:

Catalyst

Cp:

Cyclopentadienyl

DABCO:

1,4-Diazabicyclo[2.2.2]octane

DET:

Diethyl tartrate

DIBALH:

Diisobutylaluminum hydride

DMAP:

4-(Dimethylamino)pyridine

DBU:

1,8-Diazabicyclo[4.3.0]undec-7-ene

DEAD:

Diethyl azodicarboxylate

DME:

1,2-Dimethoxyethane

DMF:

Dimethylformamide

DMSO:

Dimethyl sulfoxide

ee:

Enantiomer excess

equiv:

Equivalent(s)

Et:

Ethyl

h:

Hour(s)

HMPA:

Hexamethylphosphoric triamide

LDA:

Lithium diisopropylamide

m-CPBA:

m-Chloroperoxybenzoic acid

Me:

Methyl

Mes:

Mesityl, 2,4,6-trimethylphenyl

min:

Minute(s)

NaHMDS:

Sodium hexamethyldisilazide

NBS:

N-Bromosuccinimide

Nu:

Nucleophile

PDC:

Pyridinium dichromate

Ph:

Phenyl

PPTS:

Pyridinium p-toluenesulfonate

rt:

Room temperature

Tf:

Trifluoromethanesulfonyl (triflyl)

THF:

Tetrahydrofuran

THP:

Tetrahydropyran-2-yl

TMEDA:

N,N,N′,N′-Tetramethyl-1,2-ethylenediamine

TMS:

Trimethylsilyl

Ts:

Tosyl, 4-Toluenesulfonyl

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  1. Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, 93053, Regensburg, Germany

    Rakeshwar Bandichhor, Bernd Nosse & Oliver Reiser

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  1. Rakeshwar Bandichhor
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  2. Bernd Nosse
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  3. Oliver Reiser
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Correspondence to Oliver Reiser .

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Bandichhor, R., Nosse, B., Reiser, O. Paraconic Acids—The Natural Products from Lichen Symbiont. In: Natural Product Synthesis I. Topics in Current Chemistry, vol 243. Springer, Berlin, Heidelberg. https://doi.org/10.1007/b96881

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