Using Singlet Oxygen to Synthesize Polyoxygenated Natural Products from Furans

Using singlet oxygen to synthesize polyoxygenated natural products from furans.

[Reaction: see text]. Singlet oxygen is a powerful tool in the armament of the synthetic organic chemist and possibly in that of nature itself. In this Account, we illustrate a small selection of the many ways singlet oxygen can be harnessed in the laboratory to aid in the construction of the complex molecular motifs found in natural products. A more philosophical question is also addressed: na...

Using Singlet Oxygen to Synthesize Natural Products and Drugs.

This Review describes singlet oxygen ((1)O2) in the organic synthesis of targets on possible (1)O2 biosynthetic routes. The visible-light sensitized production of (1)O2 is not only useful for synthesis; it is extremely common in nature. This Review is intended to draw a logical link between flow and batch reactions-a combination that leads to the current state of (1)O2 in synthesis.

Singlet-oxygen-mediated one-pot synthesis of 3-keto-tetrahydrofurans from 2-(beta-hydroxyalkyl) furans.

Photooxygenation of 2-(beta-hydroxyalkyl) furans affords, in one synthetic operation and in high yields, 3-keto-tetrhydrofuran motifs via intramolecular Michael-type addition to the 1,4-enedione intermediate.

Singlet Oxygen

Singlet oxygen (O2) is a higher energy state molecular oxygen species. It is one of the most active intermediates involved in chemical and biochemical reactions. To fully appreciate the reactivity of O2, it is necessary to understand its physical and chemical nature. This paper reviews the generation, quenching and detection of O2. Its properties, possible chemical reactions are presented as we...

Singlet oxygen producing sensitizers: from molecular photophysics to photofunctional materials