Eight-step total synthesis of (+)-crambescin A

(+)-Crambescin A belongs to the polycyclic guanidine natural product family and has been shown to possess various medically important properties. The chiral bicyclic guanidine structure of (+)-crambescin A presents a challenge for chemical synthesis. Here we implement a novel asymmetric Biginelli re...

Descripción completa

Detalles Bibliográficos
Autores principales: Gao, Zhenhua, Li, Junchen, Song, Yunyang, Bi, Xiaojing, Meng, Xiangyan, Guo, Yongbiao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9057376/
https://www.ncbi.nlm.nih.gov/pubmed/35518432
http://dx.doi.org/10.1039/d0ra08726b
_version_ 1784697884672786432
author Gao, Zhenhua
Li, Junchen
Song, Yunyang
Bi, Xiaojing
Meng, Xiangyan
Guo, Yongbiao
author_facet Gao, Zhenhua
Li, Junchen
Song, Yunyang
Bi, Xiaojing
Meng, Xiangyan
Guo, Yongbiao
author_sort Gao, Zhenhua
collection PubMed
description (+)-Crambescin A belongs to the polycyclic guanidine natural product family and has been shown to possess various medically important properties. The chiral bicyclic guanidine structure of (+)-crambescin A presents a challenge for chemical synthesis. Here we implement a novel asymmetric Biginelli reaction strategy to achieve the enantiospecific total synthesis of (+)-crambescin A in only 8 steps from the abundant and inexpensive aliphatic aldehyde, urea and methyl 3-oxobutanoate.
format Online
Article
Text
id pubmed-9057376
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90573762022-05-04 Eight-step total synthesis of (+)-crambescin A Gao, Zhenhua Li, Junchen Song, Yunyang Bi, Xiaojing Meng, Xiangyan Guo, Yongbiao RSC Adv Chemistry (+)-Crambescin A belongs to the polycyclic guanidine natural product family and has been shown to possess various medically important properties. The chiral bicyclic guanidine structure of (+)-crambescin A presents a challenge for chemical synthesis. Here we implement a novel asymmetric Biginelli reaction strategy to achieve the enantiospecific total synthesis of (+)-crambescin A in only 8 steps from the abundant and inexpensive aliphatic aldehyde, urea and methyl 3-oxobutanoate. The Royal Society of Chemistry 2020-10-26 /pmc/articles/PMC9057376/ /pubmed/35518432 http://dx.doi.org/10.1039/d0ra08726b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Gao, Zhenhua
Li, Junchen
Song, Yunyang
Bi, Xiaojing
Meng, Xiangyan
Guo, Yongbiao
Eight-step total synthesis of (+)-crambescin A
title Eight-step total synthesis of (+)-crambescin A
title_full Eight-step total synthesis of (+)-crambescin A
title_fullStr Eight-step total synthesis of (+)-crambescin A
title_full_unstemmed Eight-step total synthesis of (+)-crambescin A
title_short Eight-step total synthesis of (+)-crambescin A
title_sort eight-step total synthesis of (+)-crambescin a
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9057376/
https://www.ncbi.nlm.nih.gov/pubmed/35518432
http://dx.doi.org/10.1039/d0ra08726b
work_keys_str_mv AT gaozhenhua eightsteptotalsynthesisofcrambescina
AT lijunchen eightsteptotalsynthesisofcrambescina
AT songyunyang eightsteptotalsynthesisofcrambescina
AT bixiaojing eightsteptotalsynthesisofcrambescina
AT mengxiangyan eightsteptotalsynthesisofcrambescina
AT guoyongbiao eightsteptotalsynthesisofcrambescina

Ejemplares similares