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Carbohydrate-Derived Spiroketals and Spirocyclic Lactones

  • Perali Ramu SridharEmail author
Chapter
Part of the Topics in Heterocyclic Chemistry book series

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.

Keywords

Bicycles bis-C,C-glycosides Endo-glycals Exo-glycals Natural products 

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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© Springer Nature Switzerland AG 2019

Authors and Affiliations

  1. 1.School of ChemistryUniversity of HyderabadHyderabadIndia

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