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. 2007 Aug 16;9(17):3229-32.
doi: 10.1021/ol0710257. Epub 2007 Jul 24.

Synthesis of resorcinol derived spironitronates

Maurice A Marsini  1 , Yaodong Huang, Ryan W Van De Water, Thomas R R Pettus
Affiliations

Synthesis of resorcinol derived spironitronates

Maurice A Marsini et al. Org Lett. .

Abstract

Syntheses of several unique spironitronates are reported. The key transformation involves the first known example of an ipso oxidative cyclization of nitro functionality. Oxidation proceeds from both o- and p-phenols. Reductions of these compounds provide novel spiroisoxazoline derivatives.

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Figures

Figure 1
Figure 1
Biosynthesis of spiroisoxazoline derivatives.
Scheme 1
Scheme 1
Unanticipated Spironitronate Formation
Scheme 2
Scheme 2
General Synthesis of p-Quinol Spironitronates
Scheme 3
Scheme 3
Stereoselective 1,4-Addition and Reduction of 11
Scheme 4
Scheme 4
Other Transformations of 11
Scheme 5
Scheme 5
General Synthesis of o-Quinol Spironitronates
See this image and copyright information in PMC

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