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Literature DB >> 18399410

Intermolecular radical addition reactions of alpha-iodo cycloalkenones and a synthetic study of the formal synthesis of enantiopure fawcettimine.

Kuan-Miao Liu¹, Chi-Min Chau, Chin-Kang Sha.

Abstract

The generation of alpha-carbonyl vinyl radicals from alpha-iodo cycloalkenones, the scope of their participation in intermolecular addition reactions with electron-withdrawing olefins are studied and a synthetic study of the formal synthesis of enantiopure fawcettimine using this reaction is described.

Entities: Chemical

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Year: 2008 PMID： 18399410 DOI： 10.1039/b714078a

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

6 in total

1. Total synthesis of the Lycopodium alkaloid serratezomine A using free radical-mediated vinyl amination to prepare a β-stannyl enamine linchpin.

Authors: Julie A Pigza; Jeong-Seok Han; Aroop Chandra; Daniel Mutnick; Maren Pink; Jeffrey N Johnston
Journal: J Org Chem Date: 2012-12-28 Impact factor: 4.354

2. Total synthesis of (+)-complanadine A using an iridium-catalyzed pyridine C-H functionalization.

Authors: Daniel F Fischer; Richmond Sarpong
Journal: J Am Chem Soc Date: 2010-05-05 Impact factor: 15.419

3. Unified total syntheses of fawcettimine class alkaloids: fawcettimine, fawcettidine, lycoflexine, and lycoposerramine B.

Authors: Guojun Pan; Robert M Williams
Journal: J Org Chem Date: 2012-05-07 Impact factor: 4.354

Intermolecular radical addition reactions of alpha-iodo cycloalkenones and a synthetic study of the formal synthesis of enantiopure fawcettimine.

1. Total synthesis of the Lycopodium alkaloid serratezomine A using free radical-mediated vinyl amination to prepare a β-stannyl enamine linchpin.

2. Total synthesis of (+)-complanadine A using an iridium-catalyzed pyridine C-H functionalization.

3. Unified total syntheses of fawcettimine class alkaloids: fawcettimine, fawcettidine, lycoflexine, and lycoposerramine B.

4. Synthesis of cis-hydrindan-2,4-diones bearing an all-carbon quaternary center by a Danheiser annulation.

5. Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids.

6. Construction of spirocarbocycles via gold-catalyzed intramolecular dearomatization of naphthols.