Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture

[Image: see text] The enantiomers of the natural product cycloprodigiosin were prepared using an expedient five-step synthetic sequence that takes advantage of a Schöllkopf–Barton–Zard (SBZ) pyrrole annulation with a chiral isocyanoacetate and a nitrocyclohexene derivative. Using chiral HPLC and X-r...

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Autores principales: Johnson, Rebecca E., de Rond, Tristan, Lindsay, Vincent N. G., Keasling, Jay D., Sarpong, Richmond
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4509414/
https://www.ncbi.nlm.nih.gov/pubmed/26114660
http://dx.doi.org/10.1021/acs.orglett.5b01527
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author Johnson, Rebecca E.
de Rond, Tristan
Lindsay, Vincent N. G.
Keasling, Jay D.
Sarpong, Richmond
author_facet Johnson, Rebecca E.
de Rond, Tristan
Lindsay, Vincent N. G.
Keasling, Jay D.
Sarpong, Richmond
author_sort Johnson, Rebecca E.
collection PubMed
description [Image: see text] The enantiomers of the natural product cycloprodigiosin were prepared using an expedient five-step synthetic sequence that takes advantage of a Schöllkopf–Barton–Zard (SBZ) pyrrole annulation with a chiral isocyanoacetate and a nitrocyclohexene derivative. Using chiral HPLC and X-ray crystallographic analyses of the synthetically prepared material and natural isolate (isolated from the marine bacterium Pseudoalteromonas rubra), naturally occurring cycloprodigiosin was determined to be a scalemic mixture occurring in an enantiomeric ratio of 83:17 (R)/(S) at C4′.
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spelling pubmed-45094142015-07-22 Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture Johnson, Rebecca E. de Rond, Tristan Lindsay, Vincent N. G. Keasling, Jay D. Sarpong, Richmond Org Lett [Image: see text] The enantiomers of the natural product cycloprodigiosin were prepared using an expedient five-step synthetic sequence that takes advantage of a Schöllkopf–Barton–Zard (SBZ) pyrrole annulation with a chiral isocyanoacetate and a nitrocyclohexene derivative. Using chiral HPLC and X-ray crystallographic analyses of the synthetically prepared material and natural isolate (isolated from the marine bacterium Pseudoalteromonas rubra), naturally occurring cycloprodigiosin was determined to be a scalemic mixture occurring in an enantiomeric ratio of 83:17 (R)/(S) at C4′. American Chemical Society 2015-06-26 2015-07-17 /pmc/articles/PMC4509414/ /pubmed/26114660 http://dx.doi.org/10.1021/acs.orglett.5b01527 Text en Copyright © 2015 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 Johnson, Rebecca E.
de Rond, Tristan
Lindsay, Vincent N. G.
Keasling, Jay D.
Sarpong, Richmond
Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture
title Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture
title_full Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture
title_fullStr Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture
title_full_unstemmed Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture
title_short Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture
title_sort synthesis of cycloprodigiosin identifies the natural isolate as a scalemic mixture
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4509414/
https://www.ncbi.nlm.nih.gov/pubmed/26114660
http://dx.doi.org/10.1021/acs.orglett.5b01527
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