4-Hydroxy-6-alkyl-2-pyrones as nucleophilic coupling partners in Mitsunobu reactions and oxa-Michael additions

Michael J. Burns; Thomas O. Ronson; Richard J. K. Taylor; Ian J. S. Fairlamb

doi:10.3762/bjoc.10.116

4-Hydroxy-6-alkyl-2-pyrones as nucleophilic coupling partners in Mitsunobu reactions and oxa-Michael additions

Michael J. Burns, Thomas O. Ronson, Richard J. K. Taylor, Ian J. S. Fairlamb

Chemistry

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

Abstract

Two mild and efficient strategies have been developed for the O-functionalisation of 4-hydroxy-6-alkyl-2-pyrones, by using them as nucleophilic partners in oxa-Michael additions and the Mitsunobu reaction. The reactions proceed in moderate to excellent yields on a range of substrates containing useful functionality. The reactions serve as practical and valuable synthetic methods to construct complex 2-pyronyl ethers, which are found embedded in a number of natural products.

Original language	English
Pages (from-to)	1159-1165
Number of pages	7
Journal	Beilstein Journal of Organic Chemistry
Volume	10
DOIs	https://doi.org/10.3762/bjoc.10.116
Publication status	Published - 2014

Keywords

HETEROCYCLES
Mitsonobu
Oxa-Michael
2-PYRONES
VINYL ETHERS

Access to Document

10.3762/bjoc.10.116

Cite this

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title = "4-Hydroxy-6-alkyl-2-pyrones as nucleophilic coupling partners in Mitsunobu reactions and oxa-Michael additions",

abstract = "Two mild and efficient strategies have been developed for the O-functionalisation of 4-hydroxy-6-alkyl-2-pyrones, by using them as nucleophilic partners in oxa-Michael additions and the Mitsunobu reaction. The reactions proceed in moderate to excellent yields on a range of substrates containing useful functionality. The reactions serve as practical and valuable synthetic methods to construct complex 2-pyronyl ethers, which are found embedded in a number of natural products.",

keywords = "HETEROCYCLES, Mitsonobu, Oxa-Michael, 2-PYRONES, VINYL ETHERS",

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language = "English",

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AU - Burns, Michael J.

AU - Ronson, Thomas O.

AU - Taylor, Richard J. K.

AU - Fairlamb, Ian J. S.

PY - 2014

Y1 - 2014

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AB - Two mild and efficient strategies have been developed for the O-functionalisation of 4-hydroxy-6-alkyl-2-pyrones, by using them as nucleophilic partners in oxa-Michael additions and the Mitsunobu reaction. The reactions proceed in moderate to excellent yields on a range of substrates containing useful functionality. The reactions serve as practical and valuable synthetic methods to construct complex 2-pyronyl ethers, which are found embedded in a number of natural products.

KW - HETEROCYCLES

KW - Mitsonobu

KW - Oxa-Michael

KW - 2-PYRONES

KW - VINYL ETHERS

U2 - 10.3762/bjoc.10.116

DO - 10.3762/bjoc.10.116

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JF - Beilstein Journal of Organic Chemistry

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