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

• Marco G. Rigamonti and
• Francesco G. Gatti

Beilstein J. Org. Chem. 2015, 11, 2117–2124, doi:10.3762/bjoc.11.228

• Marco G. Rigamonti Francesco G. Gatti Chemistry Department “G. Natta”, Politecnico di Milano, Piazza Leonardo da Vinci 1, 20133 Milano, Italy 10.3762/bjoc.11.228 Abstract The first stereoselective synthesis of lippidulcines A, B and C has been accomplished starting from (+)-hernandulcin, which

• 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. Keywords: ADH ketone reduction; cooling agent; Corey–Bakshi–Shibata reduction; dehydrogenation; hernandulcin; Kornblum–DeLaMare rearrangement

• , in honor of the Spanish scientist, this natural product was called hernandulcin [6]. Hernandulcin is the first strongly sweet sesquiterpene, making it a breakthrough discovery in the field of natural sugar substitutes. It turned out that 1, which belongs to the family of bisabolanes, is more than