Elusive 6-e xo-Hydroxybicyclo[2.2.2]octan-2-ones from the Corresponding Acetates by Methanolysis in the Presence of CH3ONa/La(OTf)3

A series of 6-exo-acetoxybicyclo[2.2.2]octan-2-ones were converted into the corresponding 6-exo-hydroxybicyclo[2.2.2]octan-2-ones by methanolysis in the presence of CH3ONa/La(OTf)3. Under the given conditions, epimerization at C(6) of the latter led in the least favorable cases only to traces of the...

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Bibliographic Details
Published in:Organic letters 2002-08, Vol.4 (16), p.2783-2785
Main Authors: Di Stefano, Stefano, Leonelli, Francesca, Garofalo, Barbara, Mandolini, Luigi, Marini Bettolo, Rinaldo, Migneco, Luisa Maria
Format: Article
Language:English
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Summary:A series of 6-exo-acetoxybicyclo[2.2.2]octan-2-ones were converted into the corresponding 6-exo-hydroxybicyclo[2.2.2]octan-2-ones by methanolysis in the presence of CH3ONa/La(OTf)3. Under the given conditions, epimerization at C(6) of the latter led in the least favorable cases only to traces of the more stable 6-endo-hydroxybicyclo[2.2.2]octan-2-ones. This procedure, when combined with the described conversion of easily available 6-endo-hydroxybicyclo[2.2.2]octan-2-ones into the corresponding 6-exo-acetoxy derivatives, provides a convenient route to elusive 6-exo-hydroxybicyclo[2.2.2]octan-2-ones. Applications to total synthesis are shown and envisaged.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol026326p