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Carbohydrate-Derived Spiroketals and Spirocyclic Lactones

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Carbohydrate-spiro-heterocycles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 57))

Abstract

Various methods for the synthesis of carbohydrate-derived spiroketals and spirocyclic lactones starting from endo- and exo-glycals are discussed. Further conversion of the spiroketals and spirolactones to the natural products is also emphasized wherever applicable.

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Abbreviations

Ac:

Acetyl

Bn:

Benzyl

Bu:

Butyl

Cp:

Cyclopentadienyl

CSA:

Camphor-10-sulfonic acid

DBU:

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

DDQ:

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

DMDO:

3,3-Dimethyldioxirane

DMF:

N,N-dimethylformamide

DMP:

Dess-Martin periodinane

DMSO:

Dimethyl sulfoxide

EDA:

Ethyl diazoacetate

IBX:

2-Iodoxybenzoic acid

i-Pr:

Isopropyl

LAH:

Lithium aluminum hydride

LiDBB:

Lithium 4,4′-di-tert-butylbiphenylide

LiHMDS:

Lithium hexamethyldisilazide

mCPBA:

m-chloroperoxybenzoic acid

MDA:

Methyl diazoacetate

MS:

Molecular sieves

NBS:

N-bromosuccinimide

NIS:

N-iodosuccinimide

PMB:

p-methoxybenzyl

PPTS:

Pyridinium p-toluenesulfonate

SIBX:

Stabilized 2-iodoxybenzoic acid

TBDPS:

tert-butyldiphenylsilyl

TBS:

tert-butyldimethylsilyl

t-Bu:

tert-butyl

Tf:

Trifluoromethanesulfonyl

TFA:

Trifluoroacetic acid

THF:

Tetrahydrofuran

THP:

Tetrahydropyran-2-yl

TIPS:

Triisopropylsilyl

TMEDA:

N,N,N′,N′-tetramethylethylenediamine

TMS:

Trimethylsilyl

TMSOTf:

Trimethylsilyl trifluoromethanesulfonate

Ts:

p-toluenesulfonyl

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Authors and Affiliations

  1. School of Chemistry, University of Hyderabad, Hyderabad, Telangana, India

    Perali Ramu Sridhar

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Correspondence to Perali Ramu Sridhar .

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  1. Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary

    László Somsák

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Sridhar, P.R. (2019). Carbohydrate-Derived Spiroketals and Spirocyclic Lactones. In: Somsák, L. (eds) Carbohydrate-spiro-heterocycles. Topics in Heterocyclic Chemistry, vol 57. Springer, Cham. https://doi.org/10.1007/7081_2019_32

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