ORCID Profile
0000-0003-4606-9831
Current Organisation
The University of Auckland
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Publisher: Elsevier BV
Date: 06-2021
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D0NP00021C
Abstract: Extremophiles continue to capture attention. This update highlights the structures of novel molecules isolated from extremophilic and extreme-tolerant microorganisms in the last decade.
Publisher: Elsevier BV
Date: 06-2008
DOI: 10.1016/J.BMC.2008.04.037
Abstract: The naturally occurring phthalide-containing antibiotics spirolaxine methyl ether, CJ-12,954, CJ-13,013, CJ-13,015, CJ-13,102, CJ-13,103, CJ-13,104 and CJ-13,108, have been reported to exhibit anti-H. pylori activity. However, the exact stereochemistry of spirolaxine methyl ether, CJ-12,954 or CJ-13,013, contributing to this observed activity has not been confirmed. The anti-H. pylori activity of several analogues of spirolaxine methyl ether, CJ-12,954 and CJ-13,013 of defined stereochemistry together with the anti-H. pylori activity of several indole analogues of the simpler phthalide-containing antibiotics CJ-13,102, CJ-13,104, CJ-13,108 and CJ-13,015 is reported herein. A 1:1 mixture of spiroacetals 5b and 6b in which the phthalide substituent exhibited (3R)-stereochemistry was sixty times more active than the corresponding 1:1 mixture of spiroacetals with (3S)-stereochemistry. Notably, the unnatural (2''S)-diastereomer of spirolaxine methyl ether exhibited more potent anti-H. pylori activity than the natural product spirolaxine methyl ether. The 4,6-dimethoxyindoles 9, 10, 11 and 13 were all found to be less active than their parent compounds 1, 2, 3 and 4, respectively. Chain-shortened 4,6-dimethoxyindole analogue 12 of CJ-13,108 3 and 4,6-dimethoxyindole-spiroacetal 13 exhibited weak anti-H. pylori activity thus providing future opportunity for drug discovery programs.
Publisher: Elsevier BV
Date: 06-2007
Publisher: Royal Society of Chemistry (RSC)
Date: 2010
DOI: 10.1039/B911514P
Publisher: Wiley
Date: 07-09-2020
Publisher: Wiley
Date: 14-12-2020
Abstract: Callyspongiolide, a macrolide natural product with a conjugated diene‐ynic side chain, has garnered significant attention from the synthetic community since its isolation from a sea sponge in 2013. Herein, the approaches that have been applied to this bioactive natural product to date are reviewed. These synthetic endeavors have established the absolute stereochemistry of this molecule and allowed further investigation into its promising caspase‐independent bioactivity, while also contributing to the wider field of macrolide synthesis.
Publisher: American Chemical Society (ACS)
Date: 05-08-2021
DOI: 10.1021/ACS.JNATPROD.1C00502
Abstract: The first total synthesis of the benzannulated 5,5-spiroketal natural products paeciloketal B and 1-
Publisher: American Chemical Society (ACS)
Date: 28-11-2011
DOI: 10.1021/JO201988M
Abstract: The full details of our enantioselective formal synthesis of the biologically active natural product berkelic acid are described. The insertion of the C-18 methyl group proved challenging, with three different approaches investigated to install the correct stereochemistry. Our initial Horner-Wadsworth-Emmons/oxa-Michael approach to the berkelic acid core proved unsuccessful upon translation to the natural product itself. However, addition of a silyl enol ether to an oxonium ion, followed by a one-pot debenzylation/spiroketalisation/thermodynamic equilibration procedure, afforded the tetracyclic structure of the berkelic acid core as a single diastereoisomer.
Publisher: Walter de Gruyter GmbH
Date: 31-10-2011
Abstract: Studies toward the synthesis of three biologically active [5,6]-benzannulated spiroketal natural products are described. The first total synthesis of paecilospirone is reported, employing a late-stage, pH-neutral spiroketalization. A formal synthesis of γ-rubromycin is described, where the spiroketal moiety is formed by delicate manipulation of the electronic properties of the spirocyclization precursor. Finally, model work toward the total synthesis of berkelic acid is summarized, introducing a novel Horner–Wadsworth–Emmons/oxa-Michael (HWE/oxa-M) cascade to access the spiroketal precursor.
Publisher: Georg Thieme Verlag KG
Date: 04-04-2011
Publisher: Royal Society of Chemistry (RSC)
Date: 2010
DOI: 10.1039/B927219B
Abstract: The one-pot Horner-Wadsworth-Emmons/oxa-Michael cascade followed by spiroketalisation affords the tetracyclic benzannulated spiroketal core of berkelic acid, an extremophile natural product with selective activity against ovarian cancer.
Publisher: Wiley
Date: 18-05-2011
Abstract: A novel route to simple 6,5‐benzannulated spiroketal analogues has been developed. A convergent Horner–Wadsworth–Emmons olefination enabled ready assembly of the spiroketal precursors. Use of a benzyl protecting group strategy enabled an efficient one‐pot hydrogenation/deprotection/spiroketalisation process to be employed providing a robust method to access a range of substituted aromatic monobenzannulated spiroketals.
Publisher: American Chemical Society (ACS)
Date: 14-09-2011
DOI: 10.1021/OL202265G
Abstract: An enantioselective formal synthesis of berkelic acid is described. The key step involves a late-stage silyl enol ether addition to a benzannulated oxonium ion with subsequent spiroketalization leading to construction of the tetracyclic core. Thermodynamically controlled equilibration under acidic conditions affords the desired spiroketal configuration as a single diastereoisomer.
Publisher: Royal Society of Chemistry (RSC)
Date: 2009
DOI: 10.1039/B800164M
Abstract: In order to survive extremes of pH, temperature, salinity and pressure, organisms have been found to develop unique defences against their environment, leading to the biosynthesis of novel molecules ranging from simple osmolytes and lipids to complex secondary metabolites. This review highlights novel molecules isolated from microorganisms that either tolerate or favour extreme growth conditions.
Location: United Kingdom of Great Britain and Northern Ireland
Location: United Kingdom of Great Britain and Northern Ireland
Location: United Kingdom of Great Britain and Northern Ireland
No related grants have been discovered for Zoe Wilson.