TY - JOUR A1 - Rigamonti, Marco Giulio A1 - Gatti, Francesco Gilberto T1 - Stereoselective synthesis of hernandulcin, peroxylippidulcine A, lippidulcines A, B and C and taste evaluation JF - Beilstein Journal of Organic Chemistry PY - 2015/// VL - 11 SP - 2117 EP - 2124 SN - 1860-5397 DO - 10.3762/bjoc.11.228 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.11.228 KW - ADH ketone reduction KW - cooling agent KW - Corey–Bakshi–Shibata reduction KW - dehydrogenation KW - hernandulcin KW - Kornblum–DeLaMare rearrangement KW - lippidulcines KW - Saegusa–Larock N2 - 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. ER -