Formation of macrocyclic lactones in the Paternò–Büchi dimerization reaction

Furan-2-ylmethyl 2-oxoacetates 1a,b, in which the furan ring and the carbonyl moiety were embedded intramolecularly, were synthesized from commercially available furan-2-ylmethanol and their photochemical reaction (hν > 290 nm) was investigated. Twelve-membered macrocyclic lactones 2a,b with C(i)...

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Autores principales: Arimura, Junya, Mizuta, Tsutomu, Hiraga, Yoshikazu, Abe, Manabu
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3063007/
https://www.ncbi.nlm.nih.gov/pubmed/21448243
http://dx.doi.org/10.3762/bjoc.7.35
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author Arimura, Junya
Mizuta, Tsutomu
Hiraga, Yoshikazu
Abe, Manabu
author_facet Arimura, Junya
Mizuta, Tsutomu
Hiraga, Yoshikazu
Abe, Manabu
author_sort Arimura, Junya
collection PubMed
description Furan-2-ylmethyl 2-oxoacetates 1a,b, in which the furan ring and the carbonyl moiety were embedded intramolecularly, were synthesized from commercially available furan-2-ylmethanol and their photochemical reaction (hν > 290 nm) was investigated. Twelve-membered macrocyclic lactones 2a,b with C(i) symmetry including two oxetane-rings, which are the Paternò–Büchi dimerization products, were isolated in ca. 20% yield. The intramolecular cyclization products, such as 3-alkoxyoxetane and 2,7-dioxabicyclo[2.2.1]hept-5-ene derivatives, were not detected in the photolysate.
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spelling pubmed-30630072011-03-28 Formation of macrocyclic lactones in the Paternò–Büchi dimerization reaction Arimura, Junya Mizuta, Tsutomu Hiraga, Yoshikazu Abe, Manabu Beilstein J Org Chem Letter Furan-2-ylmethyl 2-oxoacetates 1a,b, in which the furan ring and the carbonyl moiety were embedded intramolecularly, were synthesized from commercially available furan-2-ylmethanol and their photochemical reaction (hν > 290 nm) was investigated. Twelve-membered macrocyclic lactones 2a,b with C(i) symmetry including two oxetane-rings, which are the Paternò–Büchi dimerization products, were isolated in ca. 20% yield. The intramolecular cyclization products, such as 3-alkoxyoxetane and 2,7-dioxabicyclo[2.2.1]hept-5-ene derivatives, were not detected in the photolysate. Beilstein-Institut 2011-02-28 /pmc/articles/PMC3063007/ /pubmed/21448243 http://dx.doi.org/10.3762/bjoc.7.35 Text en Copyright © 2011, Arimura et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Arimura, Junya
Mizuta, Tsutomu
Hiraga, Yoshikazu
Abe, Manabu
Formation of macrocyclic lactones in the Paternò–Büchi dimerization reaction
title Formation of macrocyclic lactones in the Paternò–Büchi dimerization reaction
title_full Formation of macrocyclic lactones in the Paternò–Büchi dimerization reaction
title_fullStr Formation of macrocyclic lactones in the Paternò–Büchi dimerization reaction
title_full_unstemmed Formation of macrocyclic lactones in the Paternò–Büchi dimerization reaction
title_short Formation of macrocyclic lactones in the Paternò–Büchi dimerization reaction
title_sort formation of macrocyclic lactones in the paternò–büchi dimerization reaction
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3063007/
https://www.ncbi.nlm.nih.gov/pubmed/21448243
http://dx.doi.org/10.3762/bjoc.7.35
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AT mizutatsutomu formationofmacrocycliclactonesinthepaternobuchidimerizationreaction
AT hiragayoshikazu formationofmacrocycliclactonesinthepaternobuchidimerizationreaction
AT abemanabu formationofmacrocycliclactonesinthepaternobuchidimerizationreaction

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