Publikation: Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization
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2019
Autor:innen
Powers, Zachary
Scharf, Adam
Cheng, Andrea
Yang, Feng
Himmelbauer, Martin
Mitsuhashi, Takaaki
Taniguchi, Yoshimasa
Kikuchi, Takashi
Porco, John A.
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Angewandte Chemie International Edition. Wiley-Blackwell - STM. 2019, 58(45), pp. 16141-16146. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201910710
Zusammenfassung
A biomimetic route to farnesyl pyrophosphate and dimethyl orsellinic acid (DMOA)-derived meroterpenoid scaffolds has yet to be reported despite great interest from the chemistry and biomedical research communities. A concise synthetic route with the potential to access DMOA-derived meroterpenoids is highly desirable to create a library of related compounds. Herein, we report novel dearomatization methodology followed by polyene cyclization to access DMOA-derived meroterpenoid frameworks in six steps from commercially available starting materials. Furthermore, several farnesyl alkene substrates were used to generate structurally novel, DMOA-derived meroterpenoid derivatives. DFT calculations combined with experimentation provided a rationale for the observed thermodynamic distribution of polycyclization products.
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POWERS, Zachary, Adam SCHARF, Andrea CHENG, Feng YANG, Martin HIMMELBAUER, Takaaki MITSUHASHI, Lena BARRA, Yoshimasa TANIGUCHI, Takashi KIKUCHI, John A. PORCO, 2019. Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization. In: Angewandte Chemie International Edition. Wiley-Blackwell - STM. 2019, 58(45), pp. 16141-16146. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201910710BibTex
@article{Powers2019Biomi-57688,
year={2019},
doi={10.1002/anie.201910710},
title={Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization},
number={45},
volume={58},
issn={1433-7851},
journal={Angewandte Chemie International Edition},
pages={16141--16146},
author={Powers, Zachary and Scharf, Adam and Cheng, Andrea and Yang, Feng and Himmelbauer, Martin and Mitsuhashi, Takaaki and Barra, Lena and Taniguchi, Yoshimasa and Kikuchi, Takashi and Porco, John A.}
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<dcterms:abstract xml:lang="eng">A biomimetic route to farnesyl pyrophosphate and dimethyl orsellinic acid (DMOA)-derived meroterpenoid scaffolds has yet to be reported despite great interest from the chemistry and biomedical research communities. A concise synthetic route with the potential to access DMOA-derived meroterpenoids is highly desirable to create a library of related compounds. Herein, we report novel dearomatization methodology followed by polyene cyclization to access DMOA-derived meroterpenoid frameworks in six steps from commercially available starting materials. Furthermore, several farnesyl alkene substrates were used to generate structurally novel, DMOA-derived meroterpenoid derivatives. DFT calculations combined with experimentation provided a rationale for the observed thermodynamic distribution of polycyclization products.</dcterms:abstract>
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