{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Caso A"],"funding":["Universit? degli Studi di Napoli Federico II","Seventh Framework Programme"],"pagination":["1477-1488"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC6044836"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["2(4)"],"pubmed_abstract":["A chiral pool protocol toward the synthesis of the smenamide family of natural products is described. Two stereoisomers of smenamide A, namely, <i>ent</i>-smenamide A and 16-<i>epi</i>-smenamide A were synthesized with a 2.6 and 2.5% overall yield, respectively. Their carboxylic acid moieties were assembled starting from <i>S</i>-citronellene via two Wittig reactions and a Grignard process. Its coupling with either (<i>S</i>)- or (<i>R</i>)-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."],"journal":["ACS omega"],"pubmed_title":["Studies toward the Synthesis of Smenamide A, an Antiproliferative Metabolite from <i>Smenospongia aurea</i>: Total Synthesis of <i>ent</i>-Smenamide A and 16-<i>epi</i>-Smenamide A."],"pmcid":["PMC6044836"],"funding_grant_id":["311848"],"pubmed_authors":["Costantino V","Piccialli G","Piccialli V","Mangoni A","Caso A"],"additional_accession":[]},"is_claimable":false,"name":"Studies toward the Synthesis of Smenamide A, an Antiproliferative Metabolite from <i>Smenospongia aurea</i>: Total Synthesis of <i>ent</i>-Smenamide A and 16-<i>epi</i>-Smenamide A.","description":"A chiral pool protocol toward the synthesis of the smenamide family of natural products is described. Two stereoisomers of smenamide A, namely, <i>ent</i>-smenamide A and 16-<i>epi</i>-smenamide A were synthesized with a 2.6 and 2.5% overall yield, respectively. Their carboxylic acid moieties were assembled starting from <i>S</i>-citronellene via two Wittig reactions and a Grignard process. Its coupling with either (<i>S</i>)- or (<i>R</i>)-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.","dates":{"release":"2017-01-01T00:00:00Z","publication":"2017 Apr","modification":"2025-05-29T20:28:07.743Z","creation":"2019-03-26T23:47:25Z"},"accession":"S-EPMC6044836","cross_references":{"pubmed":["30023636"],"doi":["10.1021/acsomega.7b00095"]}}