2-(Prenyloxymethyl)benzoyl (POMB) group: a new temporary protecting group removable by intramolecular cyclization |
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| Authors: | Jean-Michel Vatèle |
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| Institution: | Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), UMR 5246 CNRS, Université Lyon 1, Laboratoire de Chimie Organique 1, bât.CPE, 69622 Villeurbanne Cedex, France |
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| Abstract: | 2-(Prenyloxymethyl)benzoates can be prepared from alcohols and readily available 2-(prenyloxymethyl)benzoic acid by standard acylation techniques or by Mitsunobu reaction with inversion of configuration. The POMB group can be cleaved first by oxidative removal of the prenyl group with DDQ followed by lactonization with expulsion of the alcohol catalyzed by Yb(OTf)3. These reaction conditions are compatible with the presence of a large number of common protecting groups. |
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| Keywords: | DDQ Mitsunobu reaction Prenyl ethers Protecting groups Ytterbium triflate |
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