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Synthetic Studies of Serinolipids

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Marine Natural Products

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 58))

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Abstract

A series of serinol derivatives etherificated with a non-branched polyketide possessing a 6,8-dioxabicyclo[3.2.1]octane core was isolated from extracts of marine invertebrates, ascidian tunicates belongs to the family Didemnidae. Synthetic studies of these compounds, didemniserinolipids, cyclodidemniserinol trisulfate, and siladenoserinols, are described. The characteristics of each synthesis are in the construction of the bicyclic core from each precursor.

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Abbreviations

2,2-DMP:

2,2-Dimethoxypropane

2,6-Lut:

2,6-Lutidine

Ac:

Acetyl

BAIB:

(Diacetoxyiodo)benzene

Bn:

Benzyl

Boc:

tert-Butoxycarbonyl

brsm:

Based on recovered starting material

CSA:

Camphorsulfonic acid

DBU:

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

DCC:

Dicyclohexylcarbodiimide

DDQ:

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

DEAD :

Diethyl azodicarboxylate

DIBAL-H:

Diisobutylaluminum hydride

DIPEA:

Ethyl(diisopropyl)amine

DMAP:

4-(Dimethylamino)pyridine

DME:

1,2-Dimethoxyethane

DMF:

N,N-Dimethylformamide

DMPI:

Dess–Martin periodinane

DMSO:

Dimethyl sulfoxide

Fmoc:

9-Fluorenylmethoxycarbonyl

GPC:

Glycerophosphatidylcholine

HMPA:

Hexamethylphosphoramide

IBX:

2-Iodoxybenzoic acid

Im:

Imidazole (or imidazolyl)

KHMDS:

Potassium hexamethyldisilazide

LiHMDS:

Lithium hexamethyldisilazide

MCPBA:

m-Chloroperoxybenzoic acid

MOM:

Methoxymethyl

Ms:

Methanesulfonyl

MS:

Molecular sieves

PMB:

p-Methoxybenzyl

p-NBA:

p-Nitrobenzoic acid

Red-Al:

Sodium bis(methoxyethoxy)aluminum hydride

Su:

Succinimidyl

TBAF:

Tetrabutylammonium fluoride

TBAI:

Tetrabutylammonium iodide

TBDPS:

tert-Buthyldiphenylsilyl

TBS:

tert-Buthyldimethylsilyl

TEMPO:

2,2,6,6-Tetramethylpiperidine N-oxyl

THF:

Tetrahydrofuran

TMS:

Trimethylsilyl

Ts:

p-Toluenesulfonyl

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Acknowledgements

This chapter is dedicated to the late Prof. Qing-Wen Shi who passed away on 16th October 2020. He was scheduled to co-author this chapter with a different title.

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Authors and Affiliations

  1. Graduate School of Environmental and Life Science, Okayama University, Okayama, Japan

    Hiromasa Kiyota

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  1. Hiromasa Kiyota
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Correspondence to Hiromasa Kiyota .

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  1. Okayama University, Okayama, Japan

    Hiromasa Kiyota

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Kiyota, H. (2021). Synthetic Studies of Serinolipids. In: Kiyota, H. (eds) Marine Natural Products. Topics in Heterocyclic Chemistry, vol 58. Springer, Singapore. https://doi.org/10.1007/7081_2021_52

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