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Using ring-opening reactions of oxabicyclic compounds as a strategy in organic synthesis

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Stereoselective Heterocyclic Synthesis II

Part of the book series: Topics in Current Chemistry ((4143,volume 190))

Abstract

This chapter discusses the various methods for the preparation of oxabicyclic compounds, with an emphasis on the stereo- and enantioselective synthesis of these substances. Methods to desymmetrize meso oxabicyclic compounds are also presented. The utility of these substrates for organic synthesis is demonstrated by the many strategies available for ring-opening the bicyclic compounds to yield cyclic and acyclic structures. Examples demonstrating how this strategy has been incorporated into the efficient syntheses of many natural products are presented.

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Abbreviations

9-BBN:

9-borabicyclononane

BINAP:

2,2′-bis(diphenylphosphino)-1, l′-binaphthyl

Bz:

benzoyl

COD:

cyclooctadiene

dba:

dibenzylideneacetone

DDQ:

dichlorodicyanoquinone

DIBAL-C1:

diisobutylaluminum chloride

DIBAL-H:

diisobutylaluminum hydride

DMAD:

dimethylacetylene dicarboxylate

DME:

dimethoxyethane

dppb:

1,4-bis(diphenylphosphino)butane

HMPA:

hexamethylphosphoramide

LAH:

lithium aluminum hydride

LDA:

lithium diisopropylamide

LHMDS:

lithium hexamethyldisilazide

LiDBB:

lithium di-tert-butylbiphenylide

mCPBA:

meta-chloroperoxybenzoic acid

MS:

molecular sieves

PMB:

p-methoxybenzyl

PMP:

p-methoxyphenyl

PPTS:

pyridinium p-toluenesulfonate

pyr:

pyridine

Red-Al:

sodium bis(2-methoxyethoxy)aluminum hydride

TBDMS:

tert-butyldimethylsilyl

Tf:

trifluoromethylsulfonyl

THP:

tetrahydropyran

TMP:

2,2,6,6-tetramethylpiperidine

TMS:

trimethylsilyl

Tr:

trityl

Ts:

toluenesulfonyl

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Authors and Affiliations

  1. Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong

    Pauline Chiu

  2. Department of Chemistry, University of Toronto, M5S 1A1, Toronto, Canada

    Mark Lautens

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  1. Pauline Chiu
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  2. Mark Lautens
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Peter Metz

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Chiu, P., Lautens, M. (1997). Using ring-opening reactions of oxabicyclic compounds as a strategy in organic synthesis. In: Metz, P. (eds) Stereoselective Heterocyclic Synthesis II. Topics in Current Chemistry, vol 190. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0119245

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