Imperial College London
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Professor Philip J. Parsons

Faculty of Natural Sciences, Department of Chemistry

Senior Research Investigator
 
 
 
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Contact

 

p.parsons

 
 
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Location

 

110EMolecular Sciences Research HubWhite City Campus

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Summary

 

Publications

Citation

BibTex format

@article{Ma:2018:10.1021/acs.joc.8b02095,
author = {Ma, T-K and Elliott, DC and Reid, S and White, AJP and Parsons, PJ and Barrett, AGM},
doi = {10.1021/acs.joc.8b02095},
journal = {Journal of Organic Chemistry},
pages = {13276--13286},
title = {Meroterpenoid synthesis via sequential polyketide aromatization and cationic polyene cyclization: total syntheses of (+)-Hongoquercin A and B and related meroterpenoids.},
url = {http://dx.doi.org/10.1021/acs.joc.8b02095},
volume = {83},
year = {2018}
}
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RIS format (EndNote, RefMan)

TY  - JOUR
AB  - (+)-Hongoquercin A and B were synthesized from commercially available trans, trans-farnesol in six and eleven steps, respectively, using dual biomimetic strategies with polyketide aromatization and subsequent polyene functionalization from a common farnesyl-resorcylate intermediate. Key steps involve Pd(0)-catalyzed decarboxylative allylic rearrangement of a dioxinone β,δ-diketo ester to a β,δ-diketo dioxinone, which was readily aromatized into the corresponding resorcylate, and subsequent polyene cyclization via enantioselective protonation or regioselective terminal alkene oxidation and cationic cyclization of enantiomerically enriched epoxide to furnish the tetracyclic natural product cores. Analogues of the hongoquercin were synthesized via halonium-induced polyene cyclizations, and the meroterpenoid could be further functionalized via saponification, hydrolytic decarboxylation, reduction, and amidation reactions.
AU  - Ma,T-K
AU  - Elliott,DC
AU  - Reid,S
AU  - White,AJP
AU  - Parsons,PJ
AU  - Barrett,AGM
DO  - 10.1021/acs.joc.8b02095
EP  - 13286
PY  - 2018///
SN  - 0022-3263
SP  - 13276
TI  - Meroterpenoid synthesis via sequential polyketide aromatization and cationic polyene cyclization: total syntheses of (+)-Hongoquercin A and B and related meroterpenoids.
T2  - Journal of Organic Chemistry
UR  - http://dx.doi.org/10.1021/acs.joc.8b02095
UR  - https://www.ncbi.nlm.nih.gov/pubmed/30346765
UR  - http://hdl.handle.net/10044/1/64194
VL  - 83
ER  -
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