Stereoselective synthesis of hernandulcin, peroxylippidulcine A, lippidulcines A, B and C and taste evaluation

The first stereoselective synthesis of lippidulcines A, B and C has been accomplished starting from (+)-hernandulcin, which has been prepared on a multigram scale. The previously assigned absolute configurations have been confirmed. The key steps of this synthesis are based on a modified version of...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2015-11, Vol.11 (1), p.2117-2124
Main Authors: Rigamonti, Marco Giulio, Gatti, Francesco Gilberto
Format: Article
Language:English
Subjects:
ADH ketone reduction
Chemistry
cooling agent
Corey–Bakshi–Shibata reduction
dehydrogenation
Full Research Paper
hernandulcin
Kornblum–DeLaMare rearrangement
lippidulcines
Saegusa–Larock
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Summary:The first stereoselective synthesis of lippidulcines A, B and C has been accomplished starting from (+)-hernandulcin, which has been prepared on a multigram scale. The previously assigned absolute configurations have been confirmed. The key steps of this synthesis are based on a modified version of the Kornblum-DeLaMare rearrangement, and on a highly regioselective and stereoselective ketone reduction with the MeCBS reagent. The taste evaluations indicate that none of these sesquiterpenes are sweet, instead the lippidulcine A is a cooling agent with a mint after taste.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.11.228