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:2019:10.1021/acs.joc.9b00142,
author = {Ma, T-K and Parsons, PJ and Barrett, AGM},
doi = {10.1021/acs.joc.9b00142},
journal = {The Journal of Organic Chemistry},
pages = {4961--4970},
title = {Meroterpenoid synthesis via sequential polyketide aromatization and radical anion cascade triene cyclization: Biomimetic total syntheses of austalide natural products},
url = {http://dx.doi.org/10.1021/acs.joc.9b00142},
volume = {84},
year = {2019}
}
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RIS format (EndNote, RefMan)

TY  - JOUR
AB  - The first total synthesis of five austalide natural products, (±)-17S-dihydroaustalide K, (±)-austalide K, (±)-13-deacetoxyaustalide I, (±)-austalide P, and (±)-13-deoxyaustalide Q acid, was accomplished via a series of biomimetic transformations. Key steps involved polyketide aromatization of a trans,trans-farnesol-derived β,δ-diketodioxinone into the corresponding β-resorcylate, followed by titanium(III)-mediated reductive radical cyclization of an epoxide to furnish the drimene core. Subsequent phenylselenonium ion induced diastereoselective cyclization of the drimene completed the essential carbon framework of the austalides to access (±)-17S-dihydroaustalide K, (±)-austalide K, and (±)-13-deacetoxyaustalide I via sequential oxidations. Furthermore, (±)-13-deacetoxyaustalide I could serve as a common intermediate to be derivatized into other related natural products, (±)-austalide P and (±)-13-deoxyaustalide Q acid, by functionalizing the cyclic lactone moiety.
AU  - Ma,T-K
AU  - Parsons,PJ
AU  - Barrett,AGM
DO  - 10.1021/acs.joc.9b00142
EP  - 4970
PY  - 2019///
SN  - 0022-3263
SP  - 4961
TI  - Meroterpenoid synthesis via sequential polyketide aromatization and radical anion cascade triene cyclization: Biomimetic total syntheses of austalide natural products
T2  - The Journal of Organic Chemistry
UR  - http://dx.doi.org/10.1021/acs.joc.9b00142
UR  - http://hdl.handle.net/10044/1/69726
VL  - 84
ER  -
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