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https://hdl.handle.net/2440/52097
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Type: | Journal article |
Title: | Synthesis and Chemistry of 2,3-Dioxabicyclo[2.2.2]octane-5,6-diols |
Author: | Valente, P. Avery, T. Taylor, D. Tiekink, E. |
Citation: | Journal of Organic Chemistry, 2009; 74(1):274-282 |
Publisher: | Amer Chemical Soc |
Issue Date: | 2009 |
ISSN: | 0022-3263 1520-6904 |
Statement of Responsibility: | Peter Valente, Thomas D. Avery, Dennis K. Taylor and Edward R. T. Tiekink |
Abstract: | 1,4-Disubstituted 2,3-dioxabicyclo[2.2.2]oct-5-enes were dihydroxylated with osmium tetroxide to yield diols anti to the peroxide linkage in a highly selective manner. Reduction of the peroxide bond furnished cyclohexane-1,2,3,4-tetraols with toxocarol relative stereochemistry in excellent yield. This new methodology was employed to synthesize the natural product (1S,2R,3S,4R,5R)-2-methyl-5-(propan-2-yl)cyclohexane-1,2,3,4-tetrol (1) in a short sequence from (R)-alpha-phellandrene. Moreover, during the study of the chemistry of 2,3-dioxabicyclo[2.2.2]octane-5,6-diols a hitherto unknown rearrangement was discovered which has wide applicability for the synthesis of 1,4-dicarbonyls, including optically enriched synthons. A broad range of mechanistic investigations applicable to this rearrangement are also reported. |
Keywords: | Octanols Molecular Structure Stereoisomerism Bridged Bicyclo Compounds, Heterocyclic |
DOI: | 10.1021/jo8020506 |
Grant ID: | ARC |
Published version: | http://dx.doi.org/10.1021/jo8020506 |
Appears in Collections: | Aurora harvest 5 Chemistry publications |
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