Selective monoacylation of alkane-α,ω-diols using crude acetone powders of animal tissues

Ryszard Ostaszewski 1Dominik Koszelewski 1Marta Komar 1Adam Redzej 1Piotr Kiełbasiński 2

1. Polish Academy of Science, Institute of Organic Chemistry, Kasprzaka 44/52, Warszawa 01-224, Poland
2. Polish Academy of Sciences, Center of Molecular and Macromolecular Studies (CMMS-PAS), Sienkiewicza 112, Łódź 90-363, Poland

Abstract

Monofunctionalization of symmetrical substrates bearing two identical substituents continues to be a real challenge for organic chemists, despite a number of attempts that have been described in the literature [1]. Of particular importance is the monoacylation of polymethylene α,ω-diols, since the resulting products are crucial building blocks in the synthesis of various biologically active derivatives, e.g. insect sex pheromones [2].

In this paper a new methodology of the monoacylation of alkane-α,ω-diols will be presented, which rests upon the use of crude animal tissues (liver or kidney) acetone powders as the source of ester-forming enzymes.Clipboard.jpg

The reaction was performed in various solvents using isopropenyl acetate as the acetylating agent. It should be stressed, that certain crude acetone powders proved superior to a variety of commercially available enzymes. For example, the use of bovine liver acetone powder (BLAP) in the acetylation of octane-1,8-diol in toluene allowed to reach the 87% conversion with a monoacetylation excess of 95%. The influence of the solvents and reaction conditions on the reaction outcome will be discussed and experimental details will be presented.

Acknowledgment:

This work was supported by the network "Synthesis, Structure and Therapeutic Properties of Compounds and Organic Substances".

References:
[1] V. Framis, F. Camps, P. Clapes, Tetrahedron Lett. 2004, 45, 5031-5033 and references therein.
[2] H. Shargi, M. H. Sarvari, Tetrahedron 2003, 59, 3627-3633.

     

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    Presentation: Poster at VI Multidyscyplinarna Konferencja Nauki o Leku, by Adam Redzej
    See On-line Journal of VI Multidyscyplinarna Konferencja Nauki o Leku

    Submitted: 2008-03-13 13:00
    Revised:   2009-06-07 00:48