Synthetic Studies toward (±)-Furanocembranoid 1: Construction of the Acyclic Carbon Framework

[Image: see text] Herein, we report the synthesis of the entire acyclic carbon framework toward (±)-furanocembranoid 1 via the longest linear sequence of 12 steps from commercially available linalool and diethyl 2-isopropylmalonate. Key to the success of this synthetic approach is a silver-catalyzed...

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Autores principales: Raji Reddy, Chada, Mohammed, Siddique Z.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644170/
https://www.ncbi.nlm.nih.gov/pubmed/31458219
http://dx.doi.org/10.1021/acsomega.8b02328
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author Raji Reddy, Chada
Mohammed, Siddique Z.
author_facet Raji Reddy, Chada
Mohammed, Siddique Z.
author_sort Raji Reddy, Chada
collection PubMed
description [Image: see text] Herein, we report the synthesis of the entire acyclic carbon framework toward (±)-furanocembranoid 1 via the longest linear sequence of 12 steps from commercially available linalool and diethyl 2-isopropylmalonate. Key to the success of this synthetic approach is a silver-catalyzed enyne-annulation reaction for the formation of 2,4-disubstituted furan motif of unique furanocembranoid 1, isolated from Croton oblongifolius. Construction of macrocycle has also been explored using the ring-closing metathesis reaction.
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spelling pubmed-66441702019-08-27 Synthetic Studies toward (±)-Furanocembranoid 1: Construction of the Acyclic Carbon Framework Raji Reddy, Chada Mohammed, Siddique Z. ACS Omega [Image: see text] Herein, we report the synthesis of the entire acyclic carbon framework toward (±)-furanocembranoid 1 via the longest linear sequence of 12 steps from commercially available linalool and diethyl 2-isopropylmalonate. Key to the success of this synthetic approach is a silver-catalyzed enyne-annulation reaction for the formation of 2,4-disubstituted furan motif of unique furanocembranoid 1, isolated from Croton oblongifolius. Construction of macrocycle has also been explored using the ring-closing metathesis reaction. American Chemical Society 2018-11-16 /pmc/articles/PMC6644170/ /pubmed/31458219 http://dx.doi.org/10.1021/acsomega.8b02328 Text en Copyright © 2018 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 Raji Reddy, Chada
Mohammed, Siddique Z.
Synthetic Studies toward (±)-Furanocembranoid 1: Construction of the Acyclic Carbon Framework
title Synthetic Studies toward (±)-Furanocembranoid 1: Construction of the Acyclic Carbon Framework
title_full Synthetic Studies toward (±)-Furanocembranoid 1: Construction of the Acyclic Carbon Framework
title_fullStr Synthetic Studies toward (±)-Furanocembranoid 1: Construction of the Acyclic Carbon Framework
title_full_unstemmed Synthetic Studies toward (±)-Furanocembranoid 1: Construction of the Acyclic Carbon Framework
title_short Synthetic Studies toward (±)-Furanocembranoid 1: Construction of the Acyclic Carbon Framework
title_sort synthetic studies toward (±)-furanocembranoid 1: construction of the acyclic carbon framework
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644170/
https://www.ncbi.nlm.nih.gov/pubmed/31458219
http://dx.doi.org/10.1021/acsomega.8b02328
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