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Structural Requirements for the Thallium(III)‑mediated Cyclisation of Unsaturated Alcohols: A Novel Fragmentation Reaction Producing 19‑Norsteroids
UNIV UPPSALA, DEPT ORGAN CHEM, BOX 531, S-75121 UPPSALA, SWEDEN .
CHALMERS UNIV TECHNOL, DEPT INORGAN CHEM, S-41296 GOTHENBURG, SWEDEN .
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
1990 (English)In: Journal of the Chemical Society. Chemical communications, ISSN 0022-4936, Vol. 15, 1028-1028 p.Article in journal (Refereed) Published
Abstract [en]

The unsaturated alcohol (1) is readily cyclised to the hydroxytetrahydrofuran (3) by means of thallium(III), whereas its congener (4) has been found to give (7) as the product of a novel, stereoelectronically controlled, fragmentation; the scope of the tandem electrophilic cyclisation/solvolysis is discussed; the structure of (7) has been determined by X-ray crystallography.

Place, publisher, year, edition, pages
1990. Vol. 15, 1028-1028 p.
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Natural Sciences
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URN: urn:nbn:se:uu:diva-140730DOI: 10.1039/C39900001026OAI: oai:DiVA.org:uu-140730DiVA: diva2:384267
Available from: 2011-01-08 Created: 2011-01-08 Last updated: 2011-12-02Bibliographically approved

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Gogoll, Adolf

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