Article ; Online: Intermolecular radical cation Diels-Alder (RCDA) reaction of bicyclooctadienes: biomimetic formal total synthesis of kingianin A and total syntheses of kingianins D, F, H, and J.
The Journal of organic chemistry
2014 Volume 79, Issue 3, Page(s) 919–926
Abstract: Three endo bicyclooctadienol dimers corresponding to kingianins A and H, D, and F and J were ... without the aid of preparative HPLC. Kingianins D, F, H, and J were prepared by way of these intermediates ... prepared from one of these compounds. Completion of the synthesis of kingianin H relied on Manchand's one ...
Abstract | Three endo bicyclooctadienol dimers corresponding to kingianins A and H, D, and F and J were obtained by the intermolecular radical cation Diels-Alder (RCDA) reaction. Each isomer was cleanly isolated without the aid of preparative HPLC. Kingianins D, F, H, and J were prepared by way of these intermediates from commercially available materials in 10, 13, 9, and 17 steps, respectively. Kingianin A has already been prepared from one of these compounds. Completion of the synthesis of kingianin H relied on Manchand's one-step, three-carbon homologation. |
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MeSH term(s) | Bridged Bicyclo Compounds/chemistry ; Cations/chemistry ; Chromatography, High Pressure Liquid ; Cycloaddition Reaction ; Molecular Structure ; Polycyclic Aromatic Hydrocarbons/chemical synthesis ; Polycyclic Aromatic Hydrocarbons/chemistry ; Stereoisomerism |
Chemical Substances | Bridged Bicyclo Compounds ; Cations ; Polycyclic Aromatic Hydrocarbons ; kingianin A |
Language | English |
Publishing date | 2014-01-17 |
Publishing country | United States |
Document type | Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't |
ZDB-ID | 123490-0 |
ISSN | 1520-6904 ; 0022-3263 |
ISSN (online) | 1520-6904 |
ISSN | 0022-3263 |
DOI | 10.1021/jo402082y |
Database | MEDical Literature Analysis and Retrieval System OnLINE |
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