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Synthesis of Marine Natural Productswith Bicyclic and/or Spirocyclic Acetals

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Marine Natural Products

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 5))

Abstract

A large number of marine natural products with bicyclic and/or spirocyclic acetals have been found to date. These compounds are usually biologically active, however, synthetic studies are essential for the structure elucidation and biological application. For spirocyclic acetals in particular, it is necessary to design precursors and to control the process of dehydrative ring-closing acetal formation. Synthetic studies of four types of acetal compounds that represent recent examples are described; didemniserinolipid B (6,8-dioxabicyclo[3.2.1]octane), attenols (6,8-dioxabicyclo[3.2.1]octane or 1,6-dioxaspiro[4.5]decane), bistramides (1,7-dioxaspiro[5.5]undecane), and pinnatoxins (6,8-dioxabicyclo[3.2.1]octane and 1,7,9-trioxadispiro[5.1.5.2]pentadecane)

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Abbreviations

Alloc:

allyloxycarbonyl

DCM:

dichloromethane

AD:

asymmetric dihydroxylation

AE:

asymmetric epoxidation

cat.:

catalyst

Ipc:

isopinocamphenyl

MAO:

methylaluminoxane

MMTr:

4,4′-dimethoxytrityl

MPM:

p-methoxyphenylmethyl (PMB)

MTPA:

α-methoxy-α-phenyl-α-(trifluoromethyl)acetyl

NaHMDS:

sodium hexamethyldisilazide

NIS:

N-iodosuccinimide

NMO:

N-morphorine N-oxide

NOE:

nuclear Overhauser effect

oxi.:

oxidation

PyBOP:

benzotriazol-1-yl-oxytripyrrolidino-phosphonium hexafluorophosphate

quant.:

quantitative

Red-Al:

sodium bis(2-methoxyethoxy)aluminum hydride

SAMP:

(S)-(−)-1-amino-2-(methoxymethyl)pyrrolidine

TBAI:

tetrabutylammonium iodide

TBS:

t-butyldimethylsilyl

TEMPO:

2,2,6,6-tetramethylpiperidinyloxy radical

TES:

triethylsilyl

TPAP:

tetrapropylammonium perruthenate

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  1. Graduate School of Agricultural Science, Tohoku University, 1-1 Tsutsumidori-Amamiyamachi, 981-8555, Aoba-ku Sendai, Japan

    Hiromasa Kiyota

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  1. Hiromasa Kiyota
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Kiyota, H. Synthesis of Marine Natural Productswith Bicyclic and/or Spirocyclic Acetals. In: Kiyota, H. (eds) Marine Natural Products. Topics in Heterocyclic Chemistry, vol 5. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_029

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