Ontology highlight
ABSTRACT:
SUBMITTER: Caso A
PROVIDER: S-EPMC6044836 | biostudies-literature | 2017 Apr
REPOSITORIES: biostudies-literature
ACS omega 20170417 4
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 ...[more]