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An approach toward the triquinane-type skeleton via reagent-controlled skeletal rearrangements. A facile method for protection-deprotection of organomercurials, tuning the selectivity of Wagner-Meerwein migrations, and a new route to annulated lactones
Uppsala University.
Uppsala University.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.ORCID iD: 0000-0002-9092-261
Uppsala University.
1999 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 64, no 1, 101-119 p.101-119 p.Article in journal (Refereed) Published
Abstract [en]

Nonlinear triquinane-type building blocks have been synthesized using three strategic steps, namely, (1) Hg2+-mediated opening of a cyclopropane ring involving a skeletal rearrangement (3 --> 8), (2) an intramolecular organometallic addition across a C=O

Place, publisher, year, edition, pages
American Chemical Society (ACS), 1999. Vol. 64, no 1, 101-119 p.101-119 p.
Keyword [en]
PAUSON-KHAND REACTION; FRAGMENTATION-CYCLIZATION REACTIONS; STEREOCONTROLLED TOTAL SYNTHESIS; ENANTIOSELECTIVE TOTAL SYNTHESIS; NATURAL PRODUCT SYNTHESIS; OLEFIN COUPLING REACTIONS; FREE-RADICAL CYCLIZATIONS; BETA-KETO-ESTERS; C-H INSERTION; ANGULAR TRIQ
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-84913DOI: 10.1021/jo9812882OAI: oai:DiVA.org:uu-84913DiVA: diva2:112821
Note

Addresses: Kocovsky P, Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England. Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England. Univ Uppsala, Dept Organ Chem, S-75121 Uppsala, Sweden. Chalmers Univ Technol, Dept Inorgan Chem, S-41296 G

Available from: 2008-10-17 Created: 2008-10-17 Last updated: 2017-06-12

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Gogoll, Adolf

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