Rapid Synthesis of Polyprenylated Acylphloroglucinol Analogs via Dearomative Conjunctive Allylic Annulation

[Image: see text] Polyprenylated acylphloroglucinols (PPAPs) are structurally complex natural products with promising biological activities. Herein, we present a biosynthesis-inspired, diversity-oriented synthesis approach for rapid construction of PPAP analogs via double decarboxylative allylation...

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Autores principales: Grenning, Alexander J., Boyce, Jonathan H., Porco, John A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4140454/
https://www.ncbi.nlm.nih.gov/pubmed/25061804
http://dx.doi.org/10.1021/ja5060302
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author Grenning, Alexander J.
Boyce, Jonathan H.
Porco, John A.
author_facet Grenning, Alexander J.
Boyce, Jonathan H.
Porco, John A.
author_sort Grenning, Alexander J.
collection PubMed
description [Image: see text] Polyprenylated acylphloroglucinols (PPAPs) are structurally complex natural products with promising biological activities. Herein, we present a biosynthesis-inspired, diversity-oriented synthesis approach for rapid construction of PPAP analogs via double decarboxylative allylation (DcA) of acylphloroglucinol scaffolds to access allyl-desoxyhumulones followed by dearomative conjunctive allylic alkylation (DCAA).
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spelling pubmed-41404542015-07-25 Rapid Synthesis of Polyprenylated Acylphloroglucinol Analogs via Dearomative Conjunctive Allylic Annulation Grenning, Alexander J. Boyce, Jonathan H. Porco, John A. J Am Chem Soc [Image: see text] Polyprenylated acylphloroglucinols (PPAPs) are structurally complex natural products with promising biological activities. Herein, we present a biosynthesis-inspired, diversity-oriented synthesis approach for rapid construction of PPAP analogs via double decarboxylative allylation (DcA) of acylphloroglucinol scaffolds to access allyl-desoxyhumulones followed by dearomative conjunctive allylic alkylation (DCAA). American Chemical Society 2014-07-25 2014-08-20 /pmc/articles/PMC4140454/ /pubmed/25061804 http://dx.doi.org/10.1021/ja5060302 Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Grenning, Alexander J.
Boyce, Jonathan H.
Porco, John A.
Rapid Synthesis of Polyprenylated Acylphloroglucinol Analogs via Dearomative Conjunctive Allylic Annulation
title Rapid Synthesis of Polyprenylated Acylphloroglucinol Analogs via Dearomative Conjunctive Allylic Annulation
title_full Rapid Synthesis of Polyprenylated Acylphloroglucinol Analogs via Dearomative Conjunctive Allylic Annulation
title_fullStr Rapid Synthesis of Polyprenylated Acylphloroglucinol Analogs via Dearomative Conjunctive Allylic Annulation
title_full_unstemmed Rapid Synthesis of Polyprenylated Acylphloroglucinol Analogs via Dearomative Conjunctive Allylic Annulation
title_short Rapid Synthesis of Polyprenylated Acylphloroglucinol Analogs via Dearomative Conjunctive Allylic Annulation
title_sort rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4140454/
https://www.ncbi.nlm.nih.gov/pubmed/25061804
http://dx.doi.org/10.1021/ja5060302
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AT boycejonathanh rapidsynthesisofpolyprenylatedacylphloroglucinolanalogsviadearomativeconjunctiveallylicannulation
AT porcojohna rapidsynthesisofpolyprenylatedacylphloroglucinolanalogsviadearomativeconjunctiveallylicannulation

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