- Enantioselective synthesis of the dimeric pyranonaphthoquinone core of the cardinalins using a late-stage homocoupling strategy
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The enantioselective synthesis of a dimeric pyranonaphthoquinone closely related to the cardinalins is described. Whilst attempts to effect a double Hauser-Kraus annulation of enone 5 were unsuccessful using both bis-phthalide 4 and bis-sulfone 21, a sing
- Sperry, Jonathan,Gibson, Jennifer S.,Sejberg, Jimmy J. P.,Brimble, Margaret A.
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supporting information; experimental part
p. 4261 - 4270
(2009/02/07)
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- A facile enantioselective synthesis of the dimeric pyranonaphthoquinone core of the cardinalins
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The enantioselective synthesis of a dimeric pyranonaphthoquinone closely related to cardinalin 3 is described. Key steps include the Hauser-Kraus annulation between a cyanophthalide and a chiral enone to create the naphthalene skeleton, a Suzuki-Miyaura h
- Brimble, Margaret A.,Gibson, Jennifer S.,Sejberg, Jimmy J. P.,Sperry, Jonathan
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p. 867 - 870
(2008/12/22)
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- Rational design of inhibitors of VirA-VirG two-component signal transduction
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VirA-VirG two-component system regulates the vir (virulence) operon in response to specific host factors (xenognosins) in the plant pathogen Agrobacterium tumefaciens. Using whole cell assays, stable inhibitors inspired by the labile natural benzoxazinone inhibitor HDMBOA are developed. It is found that aromatic aldehydes represent a minimal structural unit for activity. In particular, 3-hydroxy-4,6-dimethoxy-3H-isobenzofuran-1-one (HDI) was found to have the highest activity, making it the most potent developed inhibitor of virulence gene expression in Agrobacterium.
- Maresh, Justin,Zhang, Jin,Tzeng, Yih-Ling,Goodman, Nora A.,Lynn, David G.
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p. 3281 - 3286
(2008/02/08)
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- Directed Ortho Metalation of N,N-Diethylbenzamides. Silicon Protection of Ortho Sites and the o-Methyl Group
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New general methodology of value in aromatic chemistry based on silicon protection of preferred ortho metalation sites in benzamides and o-methyl groups in o-toluamides (1, 2, Scheme I) is described.According to these methodologies, routes (Scheme II and V) to 1,2,5-, 1,2,4,5-, and 1,2,3-substituted aromatics with a variety of functionalities and oxidation states have been developed (Tables I and II).These tactics are used for the synthesis of difficult to access halo (10a-b, Scheme III) and methyl (21,25, Scheme VI) heterocycles.Ipso bromodesilylation reactions with bromine lead regiospecifically to o-bromobenzamides (12a,c, 14, Scheme IV).Walk-around-the-ring metalation processes provide highly substituted aromatics 27, 28, 29, and 30 (Scheme VII); the X-ray structure of the hexasubstituted derivative 30 shows a significant puckering of the aromatic ring.Cesium fluoride induced carbodesilylation of o-silylbenzamides with benzaldehyde affords, after TsOH cyclization, phthalides (31a-c, Scheme VIII) and constitutes a neutral alternative to the directed ortho metalation approach. α- and α,α-silylated o-toluamides are used in fluoride-mediated carbodesilylation (34a,d, Scheme IX) and desilylative Peterson olefination (35, Scheme X) procedures, respectively.The utility of α-silylated o-toluamide for the synthesis of a tetralin (38, Scheme XI) via an o-quinodimethane species is given.
- Mills, Robert J.,Taylor, Nicholas J.,Snieckus, Victor
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p. 4372 - 4385
(2007/10/02)
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- Directed Metalation of Tertiary Benzamides. Silicon Protection of Ortho Sites and Ortho Methyl Groups
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Metalation of 2-trimethylsilyl or 2-bis(trimethylsilyl)methyl benzamides occurs selectively at the 6-position, providing regiospecific routes to various trisubstituted benzenes.
- Mills, R. J.,Snieckus, V.
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p. 1565 - 1568
(2007/10/02)
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