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. 2011 Nov 2;52(44):5725-5727.
doi: 10.1016/j.tetlet.2011.08.030.

Total syntheses of isonaamine C and isonaamidine E

Heather M Lima  1 , Beatriz J Garcia-Barboza, Nicole N Khatibi, Carl J Lovely
Affiliations

Total syntheses of isonaamine C and isonaamidine E

Heather M Lima et al. Tetrahedron Lett. .

Abstract

The total syntheses of two alkaloids isolated from a marine sponge of the Leucetta sp. have been accomplished in 6 and 7 steps starting from a 4,5-diiodoimidazole derivative. Grignard mediated halogen-metal exchange was used to install the benzyl side chain. C2 substitution was accomplished via lithiation followed by quenching with trisyl azide which provided isonaamine C after hydrogenation. Isonaamidine E was then prepared from isonaamine C via introduction of the hydantoin ring by reaction with an activated parabanic acid.

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Figures

Figure 1
Figure 1
Examples of Leucetta alkaloids
Scheme 1
Scheme 1
Substitution of 4,5-diiodoimidazole
Scheme 2
Scheme 2
Grignard reaction leading to 10 and 12
Scheme 3
Scheme 3
Total synthesis of isonaamine C and isonaamidine E
See this image and copyright information in PMC

References

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    1. The nomenclature for the natural products in this manuscript follows that of the original isolation paper (see ref 4).

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