Microwave-mediated intramolecular Diels–Alder cyclization of biodihydroxylated benzoic acid derivatives
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Acknowledgements
The authors would like to thank Dr. Christian Hametner (Vienna University of Technology) for his support in NMR based structural assignment. The Ralstonia eutropha B9 mutant strain was a generous gift by Prof. Andrew G. Myers, Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts.
References and notes (16)
- et al.
Tetrahedron Lett.
(1987) - et al.
Tetrahedron Lett.
(1997) - et al.
Tetrahedron
(1978) - et al.
Tetrahedron Lett.
(1987) - et al.
Biochemistry
(1968) - et al.
Aldrichim. Acta
(1999) - et al.
J. Org. Chem.
(2002) - et al.
Biochemistry
(1971)
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