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

Michael G. Edwards; Martin N. Kenworthy; Russell R. A. Kitson; Alexis Perry; Mark S. Scott; Adrian C. Whitwood; Richard J. K. Taylor

doi:10.1002/ejoc.200800558

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

Michael G. Edwards, Martin N. Kenworthy, Russell R. A. Kitson, Alexis Perry, Mark S. Scott, Adrian C. Whitwood, Richard J. K. Taylor

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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).

Original language	English
Pages (from-to)	4769-4783
Number of pages	15
Journal	European Journal of Organic Chemistry
Issue number	28
DOIs	https://doi.org/10.1002/ejoc.200800558
Publication status	Published - Oct 2008

Keywords

tandem reactions
phosphonates
Michael addition
Horner-Wadsworth-Emmons
lactones
ONE-POT SYNTHESIS
PAEONILACTONE-B
ENANTIOSELECTIVE SYNTHESIS
STEREOSELECTIVE-SYNTHESIS
SESQUITERPENE LACTONES
TANDEM OXIDATION
ALDEHYDES
ROUTE
CORE
STEREOCHEMISTRY

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10.1002/ejoc.200800558

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Edwards, M. G., Kenworthy, M. N., Kitson, R. R. A., Perry, A., Scott, M. S., Whitwood, A. C., & Taylor, R. J. K. (2008). The preparation of alpha-alkylidene-gamma-butyrolactones using a telescoped intramolecular Michael/olefination (TIMO) sequence: Synthesis of (+)-paeonilactone B. European Journal of Organic Chemistry, (28), 4769-4783. https://doi.org/10.1002/ejoc.200800558

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title = "The preparation of alpha-alkylidene-gamma-butyrolactones using a telescoped intramolecular Michael/olefination (TIMO) sequence: Synthesis of (+)-paeonilactone B",

abstract = "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).",

keywords = "tandem reactions, phosphonates, Michael addition, Horner-Wadsworth-Emmons, lactones, ONE-POT SYNTHESIS, PAEONILACTONE-B, ENANTIOSELECTIVE SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, SESQUITERPENE LACTONES, TANDEM OXIDATION, ALDEHYDES, ROUTE, CORE, STEREOCHEMISTRY",

author = "Edwards, {Michael G.} and Kenworthy, {Martin N.} and Kitson, {Russell R. A.} and Alexis Perry and Scott, {Mark S.} and Whitwood, {Adrian C.} and Taylor, {Richard J. K.}",

year = "2008",

month = oct,

doi = "10.1002/ejoc.200800558",

language = "English",

pages = "4769--4783",

journal = "European Journal of Organic Chemistry",

issn = "1099-0690",

publisher = "Wiley-Blackwell",

number = "28",

}

The preparation of alpha-alkylidene-gamma-butyrolactones using a telescoped intramolecular Michael/olefination (TIMO) sequence: Synthesis of (+)-paeonilactone B. / Edwards, Michael G.; Kenworthy, Martin N.; Kitson, Russell R. A. et al.
In: European Journal of Organic Chemistry, No. 28, 10.2008, p. 4769-4783.

Research output: Contribution to journal › Article › peer-review

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AU - Edwards, Michael G.

AU - Kenworthy, Martin N.

AU - Kitson, Russell R. A.

AU - Perry, Alexis

AU - Scott, Mark S.

AU - Whitwood, Adrian C.

AU - Taylor, Richard J. K.

PY - 2008/10

Y1 - 2008/10

N2 - 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).

AB - 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).

KW - tandem reactions

KW - phosphonates

KW - Michael addition

KW - Horner-Wadsworth-Emmons

KW - lactones

KW - ONE-POT SYNTHESIS

KW - PAEONILACTONE-B

KW - ENANTIOSELECTIVE SYNTHESIS

KW - STEREOSELECTIVE-SYNTHESIS

KW - SESQUITERPENE LACTONES

KW - TANDEM OXIDATION

KW - ALDEHYDES

KW - ROUTE

KW - CORE

KW - STEREOCHEMISTRY

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U2 - 10.1002/ejoc.200800558

DO - 10.1002/ejoc.200800558

M3 - Article

SN - 1099-0690

SP - 4769

EP - 4783

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 28

ER -

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

Abstract

Keywords

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