ORCID Profile
0000-0003-1386-2673
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Publisher: American Chemical Society (ACS)
Date: 02-09-2011
DOI: 10.1021/OL202181G
Abstract: A structure revision for the recently isolated fungal meroterpenoids, cytosporolides A-C, is suggested based on biosynthetic speculation and reinterpretation of existing spectroscopic data. The structure revision is supported by a biomimetic synthetic study, featuring a [4 + 2] cycloaddition reaction between a presumed o-quinone methide intermediate and β-caryophyllene.
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C3OB42417K
Abstract: Protected cyclohexanol and cyclohex-2-enol substrates were efficiently and selectively oxidised by different P450cam mutants providing a general methodology for generating substituted diols using biocatalysts.
Publisher: American Chemical Society (ACS)
Date: 09-07-2013
DOI: 10.1021/OL4017832
Abstract: The total synthesis of ent-penilactone A and penilactone B has been achieved via biomimetic Michael reactions between tetronic acids and o-quinone methides. A five-component cascade reaction between a tetronic acid, formaldehyde, and a resorcinol derivative that generates four carbon-carbon bonds, one carbon-oxygen bond, and two stereocenters in a one-pot synthesis of penilactone A is also reported.
Publisher: American Chemical Society (ACS)
Date: 25-03-2021
DOI: 10.1021/JACS.1C01234
Publisher: American Chemical Society (ACS)
Date: 25-04-2023
DOI: 10.1021/JACS.3C01939
Publisher: American Chemical Society (ACS)
Date: 04-12-2015
DOI: 10.1021/ACS.ORGLETT.5B02902
Abstract: The total synthesis of peniphenones A-D has been achieved via Michael reactions between appropriate nucleophiles and a common o-quinone methide intermediate. This strategy, which was based on a biosynthetic hypothesis, minimized the use of protecting groups and thus facilitated concise syntheses of the natural products. The most complex target, the benzannulated spiroketal peniphenone A, was synthesized enantioselectively in nine linear steps from commercially available starting materials.
Publisher: Wiley
Date: 27-07-2016
Abstract: Hyperjapones A-E and hyperjaponols A-C are complex natural products of mixed aromatic polyketide and terpene biosynthetic origin that have recently been isolated from Hypericum japonicum. We have synthesized hyperjapones A-E using a biomimetic, oxidative hetero-Diels-Alder reaction to couple together dearomatized acylphloroglucinol and cyclic terpene natural products. Hyperjapone A is proposed to be the biosynthetic precursor of hyperjaponol C through a sequence of: 1) epoxidation 2) acid-catalyzed epoxide ring-opening and 3) a concerted, asynchronous alkene cyclization and 1,2-alkyl shift of a tertiary carbocation. Chemical mimicry of this proposed biosynthetic sequence allowed a concise total synthesis of hyperjaponol C to be completed in which six carbon-carbon bonds, six stereocenters, and three rings were constructed in just four steps.
Location: United Kingdom of Great Britain and Northern Ireland
No related grants have been discovered for Justin Spence.