ao7b00095_si_001.pdf (6.33 MB)
Download file

Studies toward the Synthesis of Smenamide A, an Antiproliferative Metabolite from Smenospongia aurea: Total Synthesis of ent-Smenamide A and 16-epi-Smenamide A

Download (6.33 MB)
journal contribution
posted on 17.04.2017, 08:18 by Alessia Caso, Alfonso Mangoni, Gennaro Piccialli, Valeria Costantino, Vincenzo Piccialli
A chiral pool protocol toward the synthesis of the smenamide family of natural products is described. Two stereoisomers of smenamide A, namely, ent-smenamide A and 16-epi-smenamide A were synthesized with a 2.6 and 2.5% overall yield, respectively. Their carboxylic acid moieties were assembled starting from S-citronellene via two Wittig reactions and a Grignard process. Its coupling with either (S)- or (R)-dolapyrrolidinone, synthesized from Boc-l-Phe and Boc-d-Phe, respectively, was accomplished by using the Andrus protocol. This work also established the previously unknown relative and absolute configurations of smenamide A.