Diol desymmetrization as an approach to the synthesis of unsymmetrical dienyl diesters

David J. Phillips; Kathryn S. Pillinger; Wei Li; Angela E. Taylor; Andrew E. Graham

doi:10.1016/j.tet.2007.07.089

Diol desymmetrization as an approach to the synthesis of unsymmetrical dienyl diesters

David J. Phillips, Kathryn S. Pillinger, Wei Li, Angela E. Taylor, Andrew E. Graham^*

^*Corresponding author for this work

Faculty of Computing, Engineering and Science

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

22 Citations (Scopus)

Abstract

The tandem oxidation/Wittig olefination of unactivated diols utilizing manganese dioxide produces α,β-unsaturated hydroxy esters in high yields in a highly effective desymmetrization process. The formation of small quantities of the corresponding lactones suggests that the reaction may proceed through a lactol intermediate in some cases. The α,β-unsaturated hydroxy esters are transformed into symmetrical or unsymmetrical dienyl diesters using a second oxidation/Wittig olefination sequence mediated by PCC.

Original language	English
Pages (from-to)	10528-10533
Number of pages	6
Journal	Tetrahedron Letters
Volume	63
Issue number	42
DOIs	https://doi.org/10.1016/j.tet.2007.07.089
Publication status	Published - 15 Jan 2007

Keywords

α,β-Unsaturated hydroxy esters
Diol desymmetrization
Manganese dioxide
Tandem oxidation/olefination

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10.1016/j.tet.2007.07.089Licence: CC BY-NC-ND

22 Citations
2 Doctoral Thesis

Application of Tandem Oxidation Processes to the Synthesis of Novel Oxabicycloalkane Protein Phosphatase Inhibitors
Phillips, D., 2007
Research output: Types of Thesis › Doctoral Thesis
Synthesis of Novel Cantharidin Derivatives and Evaluation of their Inhibitory Activity on Protein Phosphatase
Wei, L., 2006
Research output: Types of Thesis › Doctoral Thesis

Cite this

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title = "Diol desymmetrization as an approach to the synthesis of unsymmetrical dienyl diesters",

abstract = "The tandem oxidation/Wittig olefination of unactivated diols utilizing manganese dioxide produces α,β-unsaturated hydroxy esters in high yields in a highly effective desymmetrization process. The formation of small quantities of the corresponding lactones suggests that the reaction may proceed through a lactol intermediate in some cases. The α,β-unsaturated hydroxy esters are transformed into symmetrical or unsymmetrical dienyl diesters using a second oxidation/Wittig olefination sequence mediated by PCC. ",

keywords = "α,β-Unsaturated hydroxy esters, Diol desymmetrization, Manganese dioxide, Tandem oxidation/olefination",

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T1 - Diol desymmetrization as an approach to the synthesis of unsymmetrical dienyl diesters

AU - Phillips, David J.

AU - Pillinger, Kathryn S.

AU - Li, Wei

AU - Taylor, Angela E.

AU - Graham, Andrew E.

PY - 2007/1/15

Y1 - 2007/1/15

N2 - The tandem oxidation/Wittig olefination of unactivated diols utilizing manganese dioxide produces α,β-unsaturated hydroxy esters in high yields in a highly effective desymmetrization process. The formation of small quantities of the corresponding lactones suggests that the reaction may proceed through a lactol intermediate in some cases. The α,β-unsaturated hydroxy esters are transformed into symmetrical or unsymmetrical dienyl diesters using a second oxidation/Wittig olefination sequence mediated by PCC.

AB - The tandem oxidation/Wittig olefination of unactivated diols utilizing manganese dioxide produces α,β-unsaturated hydroxy esters in high yields in a highly effective desymmetrization process. The formation of small quantities of the corresponding lactones suggests that the reaction may proceed through a lactol intermediate in some cases. The α,β-unsaturated hydroxy esters are transformed into symmetrical or unsymmetrical dienyl diesters using a second oxidation/Wittig olefination sequence mediated by PCC.

KW - α,β-Unsaturated hydroxy esters

KW - Diol desymmetrization

KW - Manganese dioxide

KW - Tandem oxidation/olefination

U2 - 10.1016/j.tet.2007.07.089

DO - 10.1016/j.tet.2007.07.089

M3 - Article

AN - SCOPUS:34548335298

SN - 0040-4039

VL - 63

SP - 10528

EP - 10533

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 42

ER -

Diol desymmetrization as an approach to the synthesis of unsymmetrical dienyl diesters

Abstract

Keywords

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Research output

Application of Tandem Oxidation Processes to the Synthesis of Novel Oxabicycloalkane Protein Phosphatase Inhibitors

Synthesis of Novel Cantharidin Derivatives and Evaluation of their Inhibitory Activity on Protein Phosphatase

Cite this