An unusual and potentially very valuable reaction has been discovered and is viewed as providing a synthetic entry to a variety of aromatic compounds, including some natural products which express antiartheroclerotic activity (ascofuranone, khellin). This chemistry involves the generation of the previously unknown (2-alkynylethenyl)ketenes and their subsequent ring closure to zwitterionic and/or diradical intermediates. These intermediates then proceed to stable products which are either aromatic compounds or quinones. It is anticipated that this research will result in the development of methodology which will allow the regiospecific synthesis of highly substituted aromatic compounds.
| Hergueta, Antonio R; Moore, Harold W (2002) Rearrangements of cyclobutenones. Electrocyclic ring closure and thermal ring expansions of 3-allenyl- and 3-alkynyl-2-dienyl-4,4-dimethoxycyclobutenones. J Org Chem 67:1388-91 |
| Verma, S K; Nguyen, Q H; MacDougall, J M et al. (2000) Oxy-cope rearrangements of bicyclo[3.2.0]heptenones. Synthesis of bicyclo[4.2.1]non-1(4)-en-6-ones and bicyclo[5.2. 1]dec-1(10)-en-5-ones. J Org Chem 65:3379-86 |
| Verma, S K; Fleischer, E B; Moore, H W (2000) Synthesis of angular triquinanes from 1-Alkynylbicyclo[3.2. 0]hept-2-en-7-ones. A tandem alkoxy-cope ring Expansion/Transannular ring closure reaction. J Org Chem 65:8564-73 |
| Erguden, J K; Moore, H W (1999) A new tandem route to angular tetraquinanes. Synthesis of the Waihoensene ring system. Org Lett 1:375-7 |
| Avalos, J; Moore, H W; Reed, M W et al. (1989) Sensitizing potential of cyclobutenediones. Contact Dermatitis 21:341-2 |
