The preparation of α-alkylidene-γ-butyrolactones using a telescoped intramolecular Michael/olefination (TIMO) sequence:: Synthesis of (+)-paeonilactone B

被引：29

作者：

Edwards, Michael G. ^{[1
]}

Kenworthy, Martin N. ^{[1
]}

Kitson, Russell R. A. ^{[1
]}

Perry, Alexis ^{[1
]}

Scott, Mark S. ^{[1
]}

Whitwood, Adrian C. ^{[1
]}

Taylor, Richard J. K. ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 28期

基金：

英国工程与自然科学研究理事会;

关键词：

tandem reactions; phosphonates; Michael addition; Horner-Wadsworth-Emmons; lactones;

D O I：

10.1002/ejoc.200800558

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel telescoped intramolecular Michael addition/proton transfer/HWE olefination sequence has been developed to provide rapid access to alpha-alkylidene-gamma-butyrolactones. This methodology has been applied to prepare a range of tetrahydrobenzofuran-2,5-diones, and related systems, and also utilised in an extremely short synthesis of the natural product (+)-paeonilactone B in enantiomerically pure form. In addition, preliminary experiments are described that illustrate a palladium-catalysed variant proceeding by way of a pi-allyl intermediate. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：4769 / 4783

页数：15

共 9 条

[1] The telescoped intramolecular Michael/olefination (TIMO) approach to α-alkylidene-γ-butyrolactones:: Synthesis of (+)-paeonilactone B
Edwards, Michael G.
Kenworthy, Martin N.
Kitson, Russell R. A.
Scott, Mark S.
Taylor, Richard J. K.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) : 1935 - 1937
[2] A One-Pot C-H Insertion/Olefination Sequence for the Formation of α-Alkylidene-γ-butyrolactones
Lloyd, Matthew G.
Taylor, Richard J. K.
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ORGANIC LETTERS, 2014, 16 (10) : 2772 - 2775
[3] Asymmetric Synthesis of α-Alkylidene-β-hydroxy-γ-butyrolactones via Enantioselective Tandem Michael-Aldol Reaction
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JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (02): : 770 - 775
[4] Enantioselective Synthesis of α-Alkylidene-γ-Butyrolactones: Intramolecular Rauhut-Currier Reaction Promoted by Acid/Base Organocatalysts
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[5] α-Alkylidene-γ-butyrolactone synthesis via one-pot C-H insertion/olefination: substrate scope and the total synthesis of (±)-cedarmycins A and B
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[8] The formal synthesis of 3-epi jaspine B using stereoselective intramolecular oxa-Michael addition
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TETRAHEDRON-ASYMMETRY, 2010, 21 (16) : 1963 - 1970
[9] A Suzuki Cross-Coupling and Intramolecular Aza-Michael Addition Reaction Sequence Towards the Synthesis of 1,10b-epi-7-Deoxypancratistatins and Their Cytotoxicity Studies
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (34) : 5839 - 5847

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