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

[Image: see text] 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 we...

Descripción completa

Detalles Bibliográficos
Autores principales: Caso, Alessia, Mangoni, Alfonso, Piccialli, Gennaro, Costantino, Valeria, Piccialli, Vincenzo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6044836/
https://www.ncbi.nlm.nih.gov/pubmed/30023636
http://dx.doi.org/10.1021/acsomega.7b00095
_version_ 1783339553694679040
author Caso, Alessia
Mangoni, Alfonso
Piccialli, Gennaro
Costantino, Valeria
Piccialli, Vincenzo
author_facet Caso, Alessia
Mangoni, Alfonso
Piccialli, Gennaro
Costantino, Valeria
Piccialli, Vincenzo
author_sort Caso, Alessia
collection PubMed
description [Image: see text] 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.
format Online
Article
Text
id pubmed-6044836
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-60448362018-07-16 Studies toward the Synthesis of Smenamide A, an Antiproliferative Metabolite from Smenospongia aurea: Total Synthesis of ent-Smenamide A and 16-epi-Smenamide A Caso, Alessia Mangoni, Alfonso Piccialli, Gennaro Costantino, Valeria Piccialli, Vincenzo ACS Omega [Image: see text] 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. American Chemical Society 2017-04-17 /pmc/articles/PMC6044836/ /pubmed/30023636 http://dx.doi.org/10.1021/acsomega.7b00095 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Caso, Alessia
Mangoni, Alfonso
Piccialli, Gennaro
Costantino, Valeria
Piccialli, Vincenzo
Studies toward the Synthesis of Smenamide A, an Antiproliferative Metabolite from Smenospongia aurea: Total Synthesis of ent-Smenamide A and 16-epi-Smenamide A
title Studies toward the Synthesis of Smenamide A, an Antiproliferative Metabolite from Smenospongia aurea: Total Synthesis of ent-Smenamide A and 16-epi-Smenamide A
title_full Studies toward the Synthesis of Smenamide A, an Antiproliferative Metabolite from Smenospongia aurea: Total Synthesis of ent-Smenamide A and 16-epi-Smenamide A
title_fullStr Studies toward the Synthesis of Smenamide A, an Antiproliferative Metabolite from Smenospongia aurea: Total Synthesis of ent-Smenamide A and 16-epi-Smenamide A
title_full_unstemmed Studies toward the Synthesis of Smenamide A, an Antiproliferative Metabolite from Smenospongia aurea: Total Synthesis of ent-Smenamide A and 16-epi-Smenamide A
title_short Studies toward the Synthesis of Smenamide A, an Antiproliferative Metabolite from Smenospongia aurea: Total Synthesis of ent-Smenamide A and 16-epi-Smenamide A
title_sort studies toward the synthesis of smenamide a, an antiproliferative metabolite from smenospongia aurea: total synthesis of ent-smenamide a and 16-epi-smenamide a
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6044836/
https://www.ncbi.nlm.nih.gov/pubmed/30023636
http://dx.doi.org/10.1021/acsomega.7b00095
work_keys_str_mv AT casoalessia studiestowardthesynthesisofsmenamideaanantiproliferativemetabolitefromsmenospongiaaureatotalsynthesisofentsmenamideaand16epismenamidea
AT mangonialfonso studiestowardthesynthesisofsmenamideaanantiproliferativemetabolitefromsmenospongiaaureatotalsynthesisofentsmenamideaand16epismenamidea
AT piccialligennaro studiestowardthesynthesisofsmenamideaanantiproliferativemetabolitefromsmenospongiaaureatotalsynthesisofentsmenamideaand16epismenamidea
AT costantinovaleria studiestowardthesynthesisofsmenamideaanantiproliferativemetabolitefromsmenospongiaaureatotalsynthesisofentsmenamideaand16epismenamidea
AT picciallivincenzo studiestowardthesynthesisofsmenamideaanantiproliferativemetabolitefromsmenospongiaaureatotalsynthesisofentsmenamideaand16epismenamidea

Ejemplares similares