An Improved Procedure for the Synthesis of Bicyclo[2.2.2]octane- 2,6-dione

Fredrik Almqvist; Lars Eklund; Torbjörn Frejd

doi:10.1080/00397919308011243

An Improved Procedure for the Synthesis of Bicyclo[2.2.2]octane- 2,6-dione

Fredrik Almqvist, Lars Eklund, Torbjörn Frejd

Centre for Analysis and Synthesis

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

Abstract

Conjugate addition of Meldrum's acid to 2-cyclohexenone followed by direct cyclization in PPA/acetic acid constitutes a shorter, more reproducible and higher yielding route to bicyclo[2.2.2]octane-2,6-dione than previous methods. The crude dione could be used as substrate for the baker's yeast reduction to (IR, 4S, 6S)-bicyclo[2.2.2]octane-6-ol-2-one.

Original language	English
Pages (from-to)	1499-1505
Journal	Synthetic Communications
Volume	23
Issue number	11
DOIs	https://doi.org/10.1080/00397919308011243
Publication status	Published - 1993

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Subject classification (UKÄ)

Organic Chemistry

Access to Document

10.1080/00397919308011243

1 Doctoral Thesis (compilation)

Synthesis of Optically Active Bicyclo[2.2.2]octane Derivatives - A Study Towards Novel Taxol Mimics and Development of New Chiral Ligands for Asymmetric Catalysis
Almqvist, F., 1996, Organic Chemistry, Lund University. 85 p.
Research output: Thesis › Doctoral Thesis (compilation)

Cite this

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title = "An Improved Procedure for the Synthesis of Bicyclo[2.2.2]octane- 2,6-dione",

abstract = "Conjugate addition of Meldrum's acid to 2-cyclohexenone followed by direct cyclization in PPA/acetic acid constitutes a shorter, more reproducible and higher yielding route to bicyclo[2.2.2]octane-2,6-dione than previous methods. The crude dione could be used as substrate for the baker's yeast reduction to (IR, 4S, 6S)-bicyclo[2.2.2]octane-6-ol-2-one.",

author = "Fredrik Almqvist and Lars Eklund and Torbj{\"o}rn Frejd",

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AU - Almqvist, Fredrik

AU - Eklund, Lars

AU - Frejd, Torbjörn

N1 - The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

PY - 1993

Y1 - 1993

N2 - Conjugate addition of Meldrum's acid to 2-cyclohexenone followed by direct cyclization in PPA/acetic acid constitutes a shorter, more reproducible and higher yielding route to bicyclo[2.2.2]octane-2,6-dione than previous methods. The crude dione could be used as substrate for the baker's yeast reduction to (IR, 4S, 6S)-bicyclo[2.2.2]octane-6-ol-2-one.

AB - Conjugate addition of Meldrum's acid to 2-cyclohexenone followed by direct cyclization in PPA/acetic acid constitutes a shorter, more reproducible and higher yielding route to bicyclo[2.2.2]octane-2,6-dione than previous methods. The crude dione could be used as substrate for the baker's yeast reduction to (IR, 4S, 6S)-bicyclo[2.2.2]octane-6-ol-2-one.

U2 - 10.1080/00397919308011243

DO - 10.1080/00397919308011243

M3 - Article

SN - 0039-7911

VL - 23

SP - 1499

EP - 1505

JO - Synthetic Communications

JF - Synthetic Communications

IS - 11

ER -

An Improved Procedure for the Synthesis of Bicyclo[2.2.2]octane- 2,6-dione

Abstract

Bibliographical note

Subject classification (UKÄ)

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Research output

Synthesis of Optically Active Bicyclo[2.2.2]octane Derivatives - A Study Towards Novel Taxol Mimics and Development of New Chiral Ligands for Asymmetric Catalysis

Cite this