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. 2008 Jan 14;64(29):6901-6908.
doi: 10.1016/j.tet.2008.03.010.

Efficient route to 4H-1,3-oxazines through ring expansion of isoxazoles by rhodium carbenoids

James R Manning  1 , Huw M L Davies
Affiliations

Efficient route to 4H-1,3-oxazines through ring expansion of isoxazoles by rhodium carbenoids

James R Manning et al. Tetrahedron. .

Abstract

Studies related to the total synthesis of elisabethin C led to the discovery of a rhodium-catalyzed cascade sequence involving isoxazole ring expansion and a [4 + 3] cycloaddition. The scope of the isoxazole ring expansion was explored, resulting in the synthesis of a range of 4H-1,3-oxazines in 47-96% yield.

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Figures

Scheme 1
Scheme 1
Synthesis of Marine Natural Products
Scheme 2
Scheme 2
Retrosynthesis of Elisabethin C
Scheme 3
Scheme 3
Synthesis of Dihydrobenzoisoxazole 8
Scheme 4
Scheme 4
Reaction of 8 with a Vinylcarbenoid
Scheme 5
Scheme 5
Reaction of Diazoacetate 17c with Benzisoxazoles
Scheme 6
Scheme 6
Ring Expansion of an Isothiazole
Scheme 7
Scheme 7
Possible Mechanistic Pathways for Isoxazole Ring Expansion
See this image and copyright information in PMC

References

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