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.
Original language | English |
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Article number | C01610SS |
Pages (from-to) | 2308-2312 |
Number of pages | 5 |
Journal | Synthesis |
Issue number | 13 |
DOIs | |
State | Published - 2010 |
Keywords
- [2+2] cycloadditions
- cyclobutanes
- diastereoselectivity
- heterocycles
- photochemistry