From Roquefortine C to Roquefortine L: Formation of a Complex Nitrone with Simple Oxidizing Agents

The oxidation of roquefortine C to the nitrone roquefortine L was investigated using a number of different electrophilic oxidizing reagents. mCPBA and Oxone were shown to be the most effective in achieving this transformation, while unfavorable steric interactions precluded oxidation by bulky reagen...

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Bibliographic Details
Published in:Israel journal of chemistry 2017-04, Vol.57 (3-4), p.303-308
Main Authors: Gober, Claire M., Joullié, Madeleine M.
Format: Article
Language:English
Subjects:
Formations
Hydroxylation
indole alkaloid
nitrone
Oxidation
Oxidizing agents
Reagents
Roquefortine
Synthesis
Transformations
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Summary:The oxidation of roquefortine C to the nitrone roquefortine L was investigated using a number of different electrophilic oxidizing reagents. mCPBA and Oxone were shown to be the most effective in achieving this transformation, while unfavorable steric interactions precluded oxidation by bulky reagents such as Davis oxaziridine. Finally, each of the oxidants was shown to promote aromatic hydroxylation following the synthesis of the nitrone functionality.
ISSN:0021-2148
1869-5868
DOI:10.1002/ijch.201600107