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


ABSTRACT: 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.

SUBMITTER: Caso A 

PROVIDER: S-EPMC6044836 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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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.

Caso Alessia A   Mangoni Alfonso A   Piccialli Gennaro G   Costantino Valeria V   Piccialli Vincenzo V  

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]

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