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Chemistry of the Secondary Metabolites of Termites

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Progress in the Chemistry of Organic Natural Products 109

Part of the book series: Progress in the Chemistry of Organic Natural Products ((POGRCHEM,volume 109))

Abstract

Isolation, structure determination, synthesis, and biochemistry of the low-molecular-weight compounds of the secretion of exocrine glands of termites are described, with an emphasis on pheromones and defensive compounds.

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Abbreviations

% ee :

Enantiomeric excess

[α]D :

Optical rotation at λ = 589 nm

′:

Minutes

′′:

Seconds

18-crown-6:

1,4,7,10,13,16-Hexaoxacyclooctadecane

2D-NMR:

Two-dimensional nuclear magnetic resonance

8H-BINAP:

2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthalene

9-BBN:

9-Borabicyclo[3.3.1]nonane

abs:

Absolute

Ac:

Acetyl

acac:

Acetylacetonate

AIBN:

Azobisisobutyronitrile

aq:

Aqueous

ATP:

Adenosine-5′-triphosphate

ATPB:

Acetonyltriphenylphosphonium bromide

BHT:

2,6-Di-t-butyl-4-methylphenol

Bn:

Benzyl

brsm:

Based on recovered starting material

Bu:

n-Butyl

Bz:

Benzoyl

CAN:

Cerium ammonium nitrate

cat.:

Catalytic

CD:

Circular dichroism

CHC:

Cuticular hydrocarbon

COLOC:

Correlation spectrometry of long-range coupling

COSY:

Correlation spectrometry

Cp:

Cyclopentadienyl

CSA:

Camphorsulfonic acid

Cy:

Cyclohexyl

Cyt:

Cytochrome

d:

Day(s)

DABCO:

1,4-Diazabicyclo[2.2.2]octane

dba:

Dibenzylidene acetone

DBN:

1,5-Diazabicyclo[4.3.0]non-5-ene

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DCC:

1,3-Dicyclohexylcarbodiimide

DDQ:

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

DEAD:

Diethyl azodicarboxylate

DET:

Diethyl tartrate

DHF:

4,5-Dihydrofuran

DHP:

3,4-Dihydro-2H-pyran

DIAD:

Diisopropyl azodicarboxylate

DIBAH:

Diisobutylaluminum hydride

diglyme:

Bis(2-methoxyethyl) ether

DMAP:

4-(Dimethylamino)pyridine

DMAPO:

4-(Dimethylamino)pyridine oxide

DME:

1,2-Dimethoxyethane

DMF:

Dimethylformamide

DMP:

2,2-Dimethoxypropane

DMSO:

Dimethyl sulfoxide

dppp:

1,3-Bis(diphenylphosphino)propane

EDTA:

Ethylenediamine tetraacetic acid

EPC:

Enantiomerically pure compound

eq:

Equivalents

ESIMS:

Electronspray ionization mass spectrum

Et:

Ethyl

ether:

Diethyl ether

exc:

Excess

FAB:

Fast-atom bombardment

GLC:

Gas-liquid chromatography

glyme:

1,2-Dimethoxyethane (=dimethylglycol)

h:

hour

HFP:

Hexafluoropropan-2-ol

HMDS:

Hexamethyldisilazane

HMPA:

Hexamethylphosphoramide

HMQC:

Heteronuclear multiple quantum coherence

HPLC:

High-performance liquid chromatography

HRMS:

High-resolution mass spectrum

HR-TOF-MS:

High-resolution time-of-flight mass spectrum

HSQC:

Heteronuclear single-quantum correlation

hν :

Irradiation with light

IBX:

2-Iodoxybenzoic acid

IMDA:

Intramolecular Diels-Alder reaction

i-Pr:

Isopropyl

IR:

Infrared (spectroscopy)

IR-120:

Acidic ion exchange beads

KHMDS:

Potassium hexamethyldisilazide

LAH:

Lithium aluminum hydride

LDA:

Lithium diisopropylamide

LHMDS:

Lithium hexamethyldisilazide

LIS:

Lanthanide induced shift

MAD:

Methylaluminum bis-(2,6-di-t-butyl-4-methylphenoxide)

MCPBA:

m-Chloroperbenzoic acid

Me:

Methyl

MEM:

Methoxyethoxymethyl

MOM:

Methoxymethyl

MoOPH:

Oxodiperoxymolybdenum-(pyridine)-(hexamethylphosphoric triamide)

Mp:

Melting point

MPTACl:

(+)-α-Methoxy-α-(trifluormethyl)-phenylacetylchlorid (Mosher’s reagent)

MS:

Mass spectrum

Ms:

Methanesulfonyl

MS:

Molecular sieve

NaDPH:

Nicotinamide-adenine dinucleotide phosphate

NBS:

N-Bromosuccinimide

NCS:

N-Chlorosuccinimide

NMO:

Morpholine N-oxide

NMR:

Nuclear magnetic resonance (spectrometry)

NOE:

Nuclear Overhauser effect

NOESY:

Nuclear Overhauser and exchange spectroscopy

ORD:

Optical rotation dispersion (spectroscopy)

PCC:

Pyridinium chlorochromate

PDC:

Pyridinium dichromate

Ph:

Phenyl

PhCH3 :

Toluene

PhH:

Benzene

Piv:

Pivaloyl

PMB:

p-Methoxybenzyl

PMP:

p-Methoxyphenyl

PP:

Diphosphate

PPTS:

Pyridinium p-toluenesulfonate

pyr:

Pyridine

RCMT:

Ring-closing metathesis

Redal®:

Sodium bis(2-methoxyethoxy)aluminum hydride

rfl:

Reflux

rt:

Room temperature

sia:

3-Methylbut-2-yl (=siamyl)

TADA:

Transannular Diels-Alder reaction

TBAF:

Tetrabutylammonium fluoride

TBS:

t-Butyldimethylsilyl

t-Bu:

t-Butyl

TEMPO:

2,2,6,6-Tetramethylpiperidine N-oxide

t :

tertiary

TES:

Triethylsilyl

Tf (OTf):

Triflate

TFA:

Trifluoroacetic acid

TFAA:

Trifluoroacetic anhydride

thexyl:

2,3-Dimethyl-2-butyl

THF:

Tetrahydrofuran, tetrahydrofuranyl

TIPS:

Triisopropylsilyl

TLC:

Thin-layer chromatography

TMS:

Trimethylsilyl

TPAP:

Tetrapropyl perruthenate

TPS:

t-Butyldiphenylsilyl

Tr:

Trityl = triphenylmethyl

Troc:

Trichloroethoxycarbonyl

Ts:

Tosyl = p-toluenesulfonyl

UV:

Ultraviolet (spectroscopy)

y:

Year

Z:

Benzyloxycarbonyl

Δ:

High temperature

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Acknowledgment

The author thanks the editors, especially Prof. Falk for his help and patience and Prof. Kinghorn for trying to improve my meager English. Many thanks to Dr. F. Wuggenig for reading through the manuscript. Last but not least I have to thank the team of the Fernleihe of OEZBPH; without their help in providing copies of hard to attain publications, this work could never have been done.

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Authors and Affiliations

  1. Institute of Chemistry, University of Vienna, Vienna, Austria

    Edda Gössinger

  2. Mistelbach, Austria

    Edda Gössinger

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  1. Edda Gössinger
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Correspondence to Edda Gössinger .

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Editors and Affiliations

  1. College of Pharmacy, The Ohio State University, Columbus, OH, USA

    A. Douglas Kinghorn

  2. Institute of Organic Chemistry, Johannes Kepler University, Linz, Austria

    Heinz Falk

  3. UCL School of Pharmacy, University College London, Research, London, UK

    Simon Gibbons

  4. Graduate School of Pharmaceutical Sciences, Hokkaido University, Fukuoka, Japan

    Jun'ichi Kobayashi

  5. Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, Japan

    Yoshinori Asakawa

  6. School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan, China

    Ji-Kai Liu

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Gössinger, E. (2019). Chemistry of the Secondary Metabolites of Termites. In: Kinghorn, A.D., Falk, H., Gibbons, S., Kobayashi, J., Asakawa, Y., Liu, JK. (eds) Progress in the Chemistry of Organic Natural Products 109. Progress in the Chemistry of Organic Natural Products, vol 109. Springer, Cham. https://doi.org/10.1007/978-3-030-12858-6_1

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