Synthesis studies of structural analogues of tagetitoxin: 2-phosphate

Dent, Barry Roy; Furneaux, Richard H.; Gainsford, Graeme J.; Lynch, Gregory P.

doi:10.1016/s0040-4020(99)00327-0

Cited by 15 publications

(3 citation statements)

References 26 publications

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“…It consists of two, fused, six-membered rings; a tetrahydropyran in the chair conformation; and an 1,4-oxathiane in the boat conformation Dent et a!., 1999). It consists of two, fused, six-membered rings; a tetrahydropyran in the chair conformation; and an 1,4-oxathiane in the boat conformation Dent et a!., 1999).…”

Section: Spiciferonesmentioning

confidence: 99%

Phytotoxins and Plant Pathogenesis

Huang

2001

Plant Pathogenesis and Resistance

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Section: Spiciferonesmentioning

confidence: 99%

Phytotoxins and Plant Pathogenesis

Huang

2001

Plant Pathogenesis and Resistance

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“…4a To date, little work towards the synthesis of tagetitoxin has been reported. [8][9][10][11][12] We have investigated two routes for the synthesis of the proposed skeleton of tagetitoxin. One route involves nucleophilic cyclization of a thiol onto an α-dicarbonyl compound, 10,11 while the other, discussed here, uses the carbene-mediated ring expansion of a bicyclic monothioacetal, through the intermediacy of a sulfonium ylide (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Inter- and intramolecular reactions of 1-deoxy-1-thio-1,6-anhydrosugars with α-diazoesters: synthesis of the tagetitoxin core by photochemical ylide rearrangement

et al. 2012

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The one-carbon ring expansion of 1-deoxy-1-thio-1,6-anhydrosugars, mediated by metal carbenes and proceeding through the intermediacy of sulfur ylides, has been proposed as a route for the synthesis of the tagetitoxin skeleton. Intermolecular reactions of such thioanhydrosugars with diazoesters afford a range of undesired products derived from the initially formed ylide, whereas use of an intramolecular process generates stable ylides which can be converted to the tagetitoxin skeleton by photo-Stevens rearrangement. Computational studies using density functional theory indicate that the photochemical rearrangement likely proceeds through a homolysis-recombination pathway.

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“…The biological activity of tagetitoxin and the ambiguities surrounding its structure make it an intriguing target for synthesis. Recently, we completed the first synthesis of the tagetitoxin skeleton, employing as a key step the intramolecular reaction of a thiol with an α-ketoester. , In this paper, we present an alternative strategy for the synthesis of the tagetitoxin core, utilizing the rearrangement of a sulfur ylide.…”

mentioning

confidence: 99%