Semi-synthesis and insecticidal activity of dyshomoerythrine derivatives

Hart, Joanne B.; Mason, Jennifer M.; Gerard, P.J.

doi:10.1016/s0040-4020(01)01037-7

Cited by 10 publications

(7 citation statements)

References 13 publications

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“…Mesylate 20 (0.18 g, 0.35 mmol) was treated as described for compound 19 to give the title product as a light yellow oil that solidified on standing (0.064 g, 57%). A sample was recrystallized from ethyl acetate−hexanes to give colorless needles, mp 146−149 °C: 1 H and 13 C NMR spectral data identical to those already reported; HRMS (EI) m / z calcd for C 20 H 23 NO 3 (M + ) 325.1682, found 325.1682. Anal.…”

Section: Methodsmentioning

confidence: 58%

“…Dysazecine ( 1 ) is the first alkaloid having the hexahydrodibenz[ d,f ]azecine structure to have been isolated from plants . Members of this group are closely related to the widespread homoerythrinan alkaloids, for example, dyshomoerythrine ( 2 ), which occurs as the major alkaloid of Lagarostrobos colensoi (New Zealand silver pine) and exhibits bioactivity against molluscs and agriculturally important insect pests …”

Section: Introductionmentioning

confidence: 99%

“…Biosynthetically the homoerythrina alkaloids have been deemed to arise from hexahydrodibenzazecines, and this transformation can be effected in vitro . Conversely, the hexahydrodibenzazecines are obtainable from these alkaloids by acid-catalyzed cleavage of their benzylic C−N bond, and in earlier work in this laboratory, dyshomoerythrine 2 was converted to the monomethoxy dibenzazecine 4 in 55% yield by application of the Hofmann elimination reaction (N-methylation followed by heating with sodium iodide in acetone) . Related transformations have been effected under a variety of conditions. , The object of the present work was to develop methods for the preparation of a range of enantiomerically pure hexahydrodibenzazecines required for biological testing.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of the Enantiomers of Hexahydrodibenz[d,f]azecines

Furneaux¹,

Gainsford²,

Mason³

2004

J. Org. Chem.

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Suzuki coupling procedures were used to make appropriate 2-(3-aminopropyl)- 2'-(2-mesyloxy)ethyl disubstituted biphenyl derivatives 19 and 20 from which the racemic hexahydrodibenz[d,f]azecines 3 and 4 were produced following intramolecular mesyloxy displacement in dilute solution. The enantiomers of the former azecine were prepared by use of an analogue of the biphenyl aminomesylate 19 having a chiral auxiliary bound to the amino group during the closure of the 10-membered ring. Absolute configurations were assigned by X-ray diffraction analysis of compound 28.

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Section: Methodsmentioning

confidence: 58%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of the Enantiomers of Hexahydrodibenz[d,f]azecines

Furneaux¹,

Gainsford²,

Mason³

2004

J. Org. Chem.

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“…( 9 ), have not been studied for biological activity in any great detail. The alkaloid 3-epischelhammericine as well as other alkaloids from Dysoxylum have shown molluscicidal activity and cardiac effects [ 67 , 79 ], and dyshomoerythrine from Manoao is reported to have insecticidal activity [ 126 ].…”

Section: Alkaloid Diversitymentioning

confidence: 99%

Reviewing Colchicaceae Alkaloids – Perspectives of Evolution on Medicinal Chemistry

Larsson¹,

Rønsted

2013

CTMC

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The subject of chemosystematics has provided insight to both botanical classification and drug development. However, degrees of subjectivity in botanical classifications and limited understanding of the evolution of chemical characters and their biosynthetic pathways has often hampered such studies. In this review an approach of taking phylogenetic classification into account in evaluating colchicine and related phenethylisoquinoline alkaloids from the family Colchicaceae will be applied. Following on the trends of utilizing evolutionary reasoning in inferring mechanisms in eg. drug resistance in cancer and infections, this will exemplify how thinking about evolution can influence selection of plant material in drug lead discovery, and how knowledge about phylogenetic relationships may be used to evaluate predicted biosynthetic pathways.

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“…Furthermore, engagement of the one-carbon (methylene) homologue of compound 97 in an analogous sequence could provide an expeditious route to the Chomoerythrina alkaloid skeleton and perhaps, even, through suitable modification, to members of this class such as dyshomoerythrine (102). This alkaloid is derived from, inter alia, the New Zealand silver pine (Lagarostrobos colensoi) and has proven to be active against some agriculturally significant insect pests [32].…”

Section: (Iii) Approaches To the Framework Of The Erythrina And C-homentioning

confidence: 99%

Pyrroles and gem-Dihalocyclopropanes as Building Blocks for Alkaloid Synthesis

Banwell¹,

Beck²,

Stanislawski³

et al. 2005

COC

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Pyrroles and gem-dihalocyclopropanes are both readily accessible classes of compound. They have considerable potential as building blocks in the construction of alkaloid frameworks. This review details work, carried out within the authors' laboratories, directed towards such ends and with a particular emphasis on the engagement of the title moieties in intramolecular processes. An emerging area involving efforts to exploit the complementary electronic characteristics of pyrroles and gem-dihalogenocyclopropanes in the synthesis of alkaloids is also discussed.

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Semi-synthesis and insecticidal activity of dyshomoerythrine derivatives

Cited by 10 publications

References 13 publications

Synthesis of the Enantiomers of Hexahydrodibenz[d,f]azecines

Synthesis of the Enantiomers of Hexahydrodibenz[d,f]azecines

Reviewing Colchicaceae Alkaloids – Perspectives of Evolution on Medicinal Chemistry

Pyrroles and gem-Dihalocyclopropanes as Building Blocks for Alkaloid Synthesis

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