Synthesis 2010(13): 2308-2312  
DOI: 10.1055/s-0029-1218793
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

[2+2]-Photocycloaddition Reactions of Tetronic Acid Esters and Amides

Jörg P. Hehn, Diego Gamba-Sánchez, Michael Kemmler, Martin Fleck, Birte Basler, Thorsten Bach*
Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany
Fax: +49(89)28913315; e-Mail: thorsten.bach@ch.tum.de;
Further Information

Publication History

Received 15 April 2010
Publication Date:
20 May 2010 (online)

Abstract

Tetronic acid esters and amides, which are readily available from the corresponding tetronic acids, serve as useful starting materials in an intra- or intermolecular [2+2]-photocycloaddition reaction. Typical reaction conditions are irradiation at λ = 254 nm in diethyl ether or an alcohol as the solvent. The bi-, tri- or tetracyclic products so obtained can be further utilized by ring opening either of the lactone or the cyclobutane ring. Lactone ring opening led to the use of a tetramide photocycloaddition product as a conformationally restricted β-proline analogue and to an application of a tetronate photocycloaddition product in the total synthesis of punctaporonin C.

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1

Present address: BioFocus DPI AG, Gewerbestrasse 16, 4123 Allschwil, Switzerland.

2

Present address: Boehringer Ingelheim Pharma GmbH & Co. KG, Birkendorfer Straße 65, 88397 Biberach/Riß, Germany.

3

Present address: Maiwald Patentanwalts-GmbH, Elisenstraße 3, 80335 München, Germany.