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

@article{2bc965b043d64f59aed38616a7a61b48,

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",

author = "Burns, {Michael J.} and Ronson, {Thomas O.} and Taylor, {Richard J. K.} and Fairlamb, {Ian J. S.}",

year = "2014",

doi = "10.3762/bjoc.10.116",

language = "English",

volume = "10",

pages = "1159--1165",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

TY - JOUR

T1 - 4-Hydroxy-6-alkyl-2-pyrones as nucleophilic coupling partners in Mitsunobu reactions and oxa-Michael additions

AU - Burns, Michael J.

AU - Ronson, Thomas O.

AU - Taylor, Richard J. K.

AU - Fairlamb, Ian J. S.

PY - 2014

Y1 - 2014

N2 - 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.

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

M3 - Article

SN - 1860-5397

VL - 10

SP - 1159

EP - 1165

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -