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Literature DB >> 15496054

Hypervalent iodine-mediated vicinal syn diazidation: application to the total synthesis of (+/-)-dibromophakellstatin.

Raymond Chung¹, Eunsun Yu, Christopher D Incarvito, David J Austin.

Abstract

[reaction: see text] The total synthesis of (+/-)-dibromophakellstatin is described. The molecule is constructed from a key syn-diazide, formed by a hypervalent iodine-mediated diazidation of a dihydrodipyrrolopyrazinone ring structure.

Entities: Chemical Gene

Year: 2004 PMID： 15496054 DOI： 10.1021/ol0490532

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

16 in total

1. Palau'amine and related oroidin alkaloids dibromophakellin and dibromophakellstatin inhibit the human 20S proteasome.

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Journal: J Nat Prod Date: 2012-05-16 Impact factor: 4.050

2. Palladium-catalyzed direct functionalization of imidazolinone: synthesis of dibromophakellstatin.

Authors: Jianming Lu; Xianghui Tan; Chuo Chen
Journal: J Am Chem Soc Date: 2007-06-01 Impact factor: 15.419

3. Synthetic access to the chlorocyclopentane cores of the proposed original and revised structures of palau'amine.

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Review 4. Chemistry of polyvalent iodine.

Authors: Viktor V Zhdankin; Peter J Stang
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5. Generation and Reactivity of 2-Amido-1,3-diaminoallyl Cations: Cyclic Guanidine Annulations via Net (3 + 2) and (4 + 3) Cycloadditions.

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6. Syntheses of Cyclic Guanidine-Containing Natural Products.

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Review 7. Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

Authors: Ali Al-Mourabit; Manuel A Zancanella; Supriya Tilvi; Daniel Romo
Journal: Nat Prod Rep Date: 2011-05-09 Impact factor: 13.423