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Asymmetric Total Synthesis of Complex Marine Natural Products

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Book cover Marine Biotechnology II

Part of the book series: Advances in Biochemical Engineering/Biotechnology ((ABE,volume 97))

Abstract

Among nature's ecosystems, the marine environment has been an extremely rich source of structurally complex and biologically active molecules. This review aims to cover the recent developments in the synthesis of marine natural products, also reflecting the trend of their increased use to address biological questions. The examples chosen should be viewed as representative of the different structural motifs on the one hand and the strategies and stimuli for their synthesis on the other.

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Abbreviations

9-BBN:

9-borabicyclo[3.3.1]nonane

Ac:

acetyl

AIBN:

2,2′-azobis-isobutylonitrile

BEP:

2-bromo-1-ethyl-pyridinium tetrafluoroborate

BINAP:

2,2′-bis(diphenylphosphino)-1,1′-binaphthalene

BINOL:

1,1′-bi(2-naphthol)

Bn:

benzyl

Boc:

tert-butyloxycarbonyl

BOM:

benzyloxymethyl

Bz:

benzoyl

CAN:

ceric ammonium nitrate

Cbz:

benzyloxycarbonyl

Cp:

cyclopentadienyl

CSA:

10-camphorsulfonic acid

Cy:

cyclohexyl

DAST:

(diethylamino)sulphur trifluoride

dba:

trans, trans-dibenzylideneacetone

DBU:

1,8-diazabicyclo[5.4.0]undec-7-en

DDQ:

2,3-dichloro-5,6-dicyano-p-benzoquinone

de:

diastereomeric excess

DEAD:

diethyl azodicarboxylate

DHQD:

dehydroquinidine

DIAD:

di-iso-propyl azodicarboxylate

DIBALH:

di-iso-butylaluminum hydride

DIC:

N,N′-diisopropylcarbodiimide

DIP:

diisopinocampheylborane

DIPEA:

N-ethyldi-iso-propylamine

DIPS:

di-iso-propylphenylsilyl

DMAP:

N,N-(dimethylamino)pyridine

DMDO:

2,2-dimethyldioxirane

DMF:

dimethylformamide

DMP:

dimethoxypropane

DMS:

dimethylsufide

DMSO:

dimethyl sulfoxide

DPPA:

diphenylphosphoryl azide

dppf:

diphenylphosphinoferrocene

dr:

diasteremeric ratio

EDCI:

N-ethyl-N′-(3-dimethylaminopropyl) carbodiimide hydrochloride

ee:

enantiomeric excess

Fmoc:

9-fluorenylmethoxycarbonyl

HATU:

O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

HAD:

di-iso-propylamine

HMPA:

hexamethylphosphoric acid triamide

HOBT:

1-hydroxybenzotriazole

IBX:

o-iodoxybenzoic acid

imid:

imidazole

Ipc:

isopinocampheyl

KHMDS:

potassium bis(trimethylsilyl)amide

LDA:

lithium di-iso-propylamide

LiHMDS:

lithium bis(trimethylsilyl)amide

m-CPBA:

meta-chloroperbenzoic acid

MMPP:

magnesium monoperoxyphthalate

MMTr:

p-methoxyphenyldiphenylmethyl

MOM:

methoxy methyl

Ms:

methanesulfonyl

MS:

molecular sieves

NaHMDS:

sodium bis(trimethylsilyl)amide

NBS:

N-bromosuccinimide

NMM:

4-N-methylmorpholine

NMO:

N-methylmorpholin-N-oxide

NMR:

nuclear magnetic resonance

PCC:

pyridinium chlorochromate

PMB:

p-methoxybenzyl

PMBM:

p-methoxybenzyloxymethyl

PMP:

p-methoxyphenyl

PPTS:

pyridinium p-toluenesulfonate

PVP:

polyvinylpyridine

PyAOP:

7-azabenzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorphosphate

PyBroP ®:

bromotripyrrolidinophosphonium hexafluorophosphate

pyr:

pyridine

RCM:

ring closing metathesis

r.t.:

room temperature

TBAF:

tetra-n-butylammonium fluoride

TBDPS:

tert-butyldiphenylsilyl chloride

TBHP:

tert-butyl hydroperoxide

TBS:

tert-butyldimethyl silyl

TEMPO:

2,2,6,6-tetramethylpiperidine 1-oxyl

TES:

triethylsilyl

Tf:

trifluoromethanesulfonate

TFA:

trifluoroacetic acid

THF:

tetrahydrofuran

THP:

tetrahydropyranyl

TIPS:

tri-iso-propylsilyl

TMEDA:

N,N,N′,N′-tetramethylethylenediamine

TMS:

trimethyl silyl

TMSSPh:

phenylthiotrimethylsilane

tol:

tolyl

TPAP:

tetrapropylammonium perruthenate

Ts:

toluene sulfonyl

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Authors and Affiliations

  1. Institut für Organische Chemie, Universität Hannover, Schneiderberg 1B, 30167, Hannover, Germany

    Jorma Hassfeld, Markus Kalesse & Timo Stellfeld

  2. Institut für Organische Chemie, RWTH Aachen, Professor-Pirlet-Strasse 1, 52074, Aachen, Germany

    Mathias Christmann

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  1. Jorma Hassfeld
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  2. Markus Kalesse
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  4. Mathias Christmann
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Correspondence to Mathias Christmann .

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Roland Ulber Yves Le Gal

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Hassfeld, J., Kalesse, M., Stellfeld, T., Christmann, M. Asymmetric Total Synthesis of Complex Marine Natural Products. In: Ulber, R., Le Gal, Y. (eds) Marine Biotechnology II. Advances in Biochemical Engineering/Biotechnology, vol 97. Springer, Berlin, Heidelberg. https://doi.org/10.1007/b135825

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