Singlet-oxygen-mediated one-pot synthesis of 3-keto-tetrahydrofurans from 2-(beta-hydroxyalkyl) furans.
نویسندگان
چکیده
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.
منابع مشابه
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...
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All-in-one: A new and general one-pot reaction sequence initiated by singlet oxygen that transforms simple furan substrates into complex nitrogen-bearing aromatic polycycles having all the structural features of a number of important natural products (for example, the erythrina alkaloids; see scheme, RB = rose Bengal) is reported. The reaction sequence itself uses mild conditions and has wide f...
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ورودعنوان ژورنال:
- Organic letters
دوره 11 2 شماره
صفحات -
تاریخ انتشار 2009