Total Synthesis and Structure Confirmation of (E) and (Z)-Ocellenyne

[Image: see text] The (E/Z)-ocellenynes are C(15) dibrominated Laurencia natural products whose structures have been subject to several reassignments on the basis of extensive NMR analysis, biosynthetic postulates, and DFT calculations. Herein, we report the synthesis of both (E)- and (Z)-ocellenyne...

Descripción completa

Detalles Bibliográficos
Autores principales: Hicks, Harry B., Brown, Daniel S., Sam Chan, Hau Sun, Sousa, Bruno A., Christensen, Kirsten E., Burton, Jonathan W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9791679/
https://www.ncbi.nlm.nih.gov/pubmed/36508492
http://dx.doi.org/10.1021/acs.orglett.2c03524
_version_ 1784859460840194048
author Hicks, Harry B.
Brown, Daniel S.
Sam Chan, Hau Sun
Sousa, Bruno A.
Christensen, Kirsten E.
Burton, Jonathan W.
author_facet Hicks, Harry B.
Brown, Daniel S.
Sam Chan, Hau Sun
Sousa, Bruno A.
Christensen, Kirsten E.
Burton, Jonathan W.
author_sort Hicks, Harry B.
collection PubMed
description [Image: see text] The (E/Z)-ocellenynes are C(15) dibrominated Laurencia natural products whose structures have been subject to several reassignments on the basis of extensive NMR analysis, biosynthetic postulates, and DFT calculations. Herein, we report the synthesis of both (E)- and (Z)-ocellenyne, which, in combination with single crystal X-ray diffraction studies, allows their absolute configuration to be established and defines the configuration of the syn-12,13-dibromide as being (S, S) in keeping with their proposed biogenesis from the (6S, 7S)-laurediols.
format Online
Article
Text
id pubmed-9791679
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-97916792022-12-27 Total Synthesis and Structure Confirmation of (E) and (Z)-Ocellenyne Hicks, Harry B. Brown, Daniel S. Sam Chan, Hau Sun Sousa, Bruno A. Christensen, Kirsten E. Burton, Jonathan W. Org Lett [Image: see text] The (E/Z)-ocellenynes are C(15) dibrominated Laurencia natural products whose structures have been subject to several reassignments on the basis of extensive NMR analysis, biosynthetic postulates, and DFT calculations. Herein, we report the synthesis of both (E)- and (Z)-ocellenyne, which, in combination with single crystal X-ray diffraction studies, allows their absolute configuration to be established and defines the configuration of the syn-12,13-dibromide as being (S, S) in keeping with their proposed biogenesis from the (6S, 7S)-laurediols. American Chemical Society 2022-12-12 2022-12-23 /pmc/articles/PMC9791679/ /pubmed/36508492 http://dx.doi.org/10.1021/acs.orglett.2c03524 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Hicks, Harry B.
Brown, Daniel S.
Sam Chan, Hau Sun
Sousa, Bruno A.
Christensen, Kirsten E.
Burton, Jonathan W.
Total Synthesis and Structure Confirmation of (E) and (Z)-Ocellenyne
title Total Synthesis and Structure Confirmation of (E) and (Z)-Ocellenyne
title_full Total Synthesis and Structure Confirmation of (E) and (Z)-Ocellenyne
title_fullStr Total Synthesis and Structure Confirmation of (E) and (Z)-Ocellenyne
title_full_unstemmed Total Synthesis and Structure Confirmation of (E) and (Z)-Ocellenyne
title_short Total Synthesis and Structure Confirmation of (E) and (Z)-Ocellenyne
title_sort total synthesis and structure confirmation of (e) and (z)-ocellenyne
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9791679/
https://www.ncbi.nlm.nih.gov/pubmed/36508492
http://dx.doi.org/10.1021/acs.orglett.2c03524
work_keys_str_mv AT hicksharryb totalsynthesisandstructureconfirmationofeandzocellenyne
AT browndaniels totalsynthesisandstructureconfirmationofeandzocellenyne
AT samchanhausun totalsynthesisandstructureconfirmationofeandzocellenyne
AT sousabrunoa totalsynthesisandstructureconfirmationofeandzocellenyne
AT christensenkirstene totalsynthesisandstructureconfirmationofeandzocellenyne
AT burtonjonathanw totalsynthesisandstructureconfirmationofeandzocellenyne

Ejemplares similares