DOAJ Open Access 2015

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

Marco G. Rigamonti Francesco G. Gatti

Abstrak

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.

Topik & Kata Kunci

Science Organic chemistry

Penulis (2)

Marco G. Rigamonti

Francesco G. Gatti

Format Sitasi

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Rigamonti, M.G., Gatti, F.G. (2015). Stereoselective synthesis of hernandulcin, peroxylippidulcine A, lippidulcines A, B and C and taste evaluation. https://doi.org/10.3762/bjoc.11.228

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Informasi Jurnal

Tahun Terbit: 2015
Sumber Database: DOAJ
DOI: 10.3762/bjoc.11.228
Akses: Open Access ✓