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2 article(s) from Geddis, Stephen M

Synthesis and biological evaluation of 1,2-disubstituted 4-quinolone analogues of Pseudonocardia sp. natural products

Stephen M. Geddis,
Teodora Coroama,
Suzanne Forrest,
James T. Hodgkinson,
Martin Welch and
David R. Spring

Beilstein J. Org. Chem. 2018, 14, 2680–2688, doi:10.3762/bjoc.14.245

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Figure 1: A family of quinolone natural products 1–8, which were first isolated from Pseudonocardia sp. CL384...

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Scheme 1: Proposed use of the chemistry developed towards the total synthesis of 5 and 6 for generation of na...

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Scheme 2: Sonagashira coupling of alkynes 10a and 10b with commercially available acid chloride 9 to give yno...

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Scheme 3: Conjugate addition of primary amines 12a–f with ynones 11a and 11b. ^aFollowing concentration in vac...

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Scheme 4: Cyclisation of precursors 13 to natural product analogues 14 using palladium- or copper-catalysed c...

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Scheme 5: Use of an excess of DMEDA in the Cu-catalysed cyclisation of 13bb resulted in the generation of 14bg...

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Figure 2: Growth of E. coli ESS with time in the presence of 200 μM of each compound. A) Natural product seri...

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Figure 3: Growth of S. aureus 25923 with time in the presence of 200 μM of each compound. A) Natural product ...

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Figure 4: OD₅₂₀ (absorption corresponding to pyocyanin) normalised by the culture population (measured by OD₆...

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Letter

Published 19 Oct 2018

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(Z)-Selective Takai olefination of salicylaldehydes

Stephen M. Geddis,
Caroline E. Hagerman,
Warren R. J. D. Galloway,
Hannah F. Sore,
Jonathan M. Goodman and
David R. Spring

Beilstein J. Org. Chem. 2017, 13, 323–328, doi:10.3762/bjoc.13.35

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Scheme 1: A) General overview of the Takai olefination for the formation of alkenyl halides 2 from aldehydes 1...

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Scheme 2: Proposed model for the chromium(II)-mediated homologation of aldehydes to form (E)-alkenes. Hodsgon...

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Scheme 3: An unusually high level of (Z)-stereoselectivity was observed in the Takai olefination of 6. (E):(Z...

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Scheme 4: Takai olefination of meta-hydroxybenzaldehyde.

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Scheme 5: Yield for both products and residual starting material following a scaled up Takai olefination of s...

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Figure 1: Positive correlation between the amount (Z)-product and σ_m for the series of meta-halogenated salic...

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Scheme 6: Proposed mechanism for (Z)-selective Takai olefination, whereby coordination of the ortho-OH to the...

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Letter

Published 20 Feb 2017

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