Synthesis of (±)-Angustatin A: Assembly of the Phenanthrene Moiety Despite Increasing Ring Strain

[Image: see text] The synthesis of (±)-angustatin A, a phenanthrene-containing cyclophane that possesses conformational chirality, is reported. Key steps include a Pd-catalyzed Negishi coupling to assemble the necessary terphenyl intermediate, its closure into a 14-membered macrocycle via a catalyti...

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Autores principales: Doan, Hoang D., Rugen, Christian, Golz, Christopher, Alcarazo, Manuel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10563161/
https://www.ncbi.nlm.nih.gov/pubmed/37748259
http://dx.doi.org/10.1021/acs.orglett.3c02742
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author Doan, Hoang D.
Rugen, Christian
Golz, Christopher
Alcarazo, Manuel
author_facet Doan, Hoang D.
Rugen, Christian
Golz, Christopher
Alcarazo, Manuel
author_sort Doan, Hoang D.
collection PubMed
description [Image: see text] The synthesis of (±)-angustatin A, a phenanthrene-containing cyclophane that possesses conformational chirality, is reported. Key steps include a Pd-catalyzed Negishi coupling to assemble the necessary terphenyl intermediate, its closure into a 14-membered macrocycle via a catalytic-in-phosphine Wittig olefination, and finally a Pt-catalyzed alkyne hydroarylation, which is able to assemble the phenanthrene unit despite the thermodynamic cost of significantly bending arene A from the ideal plane.
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spelling pubmed-105631612023-10-11 Synthesis of (±)-Angustatin A: Assembly of the Phenanthrene Moiety Despite Increasing Ring Strain Doan, Hoang D. Rugen, Christian Golz, Christopher Alcarazo, Manuel Org Lett [Image: see text] The synthesis of (±)-angustatin A, a phenanthrene-containing cyclophane that possesses conformational chirality, is reported. Key steps include a Pd-catalyzed Negishi coupling to assemble the necessary terphenyl intermediate, its closure into a 14-membered macrocycle via a catalytic-in-phosphine Wittig olefination, and finally a Pt-catalyzed alkyne hydroarylation, which is able to assemble the phenanthrene unit despite the thermodynamic cost of significantly bending arene A from the ideal plane. American Chemical Society 2023-09-25 /pmc/articles/PMC10563161/ /pubmed/37748259 http://dx.doi.org/10.1021/acs.orglett.3c02742 Text en © 2023 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 Doan, Hoang D.
Rugen, Christian
Golz, Christopher
Alcarazo, Manuel
Synthesis of (±)-Angustatin A: Assembly of the Phenanthrene Moiety Despite Increasing Ring Strain
title Synthesis of (±)-Angustatin A: Assembly of the Phenanthrene Moiety Despite Increasing Ring Strain
title_full Synthesis of (±)-Angustatin A: Assembly of the Phenanthrene Moiety Despite Increasing Ring Strain
title_fullStr Synthesis of (±)-Angustatin A: Assembly of the Phenanthrene Moiety Despite Increasing Ring Strain
title_full_unstemmed Synthesis of (±)-Angustatin A: Assembly of the Phenanthrene Moiety Despite Increasing Ring Strain
title_short Synthesis of (±)-Angustatin A: Assembly of the Phenanthrene Moiety Despite Increasing Ring Strain
title_sort synthesis of (±)-angustatin a: assembly of the phenanthrene moiety despite increasing ring strain
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10563161/
https://www.ncbi.nlm.nih.gov/pubmed/37748259
http://dx.doi.org/10.1021/acs.orglett.3c02742
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AT golzchristopher synthesisofangustatinaassemblyofthephenanthrenemoietydespiteincreasingringstrain
AT alcarazomanuel synthesisofangustatinaassemblyofthephenanthrenemoietydespiteincreasingringstrain

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