Further Studies on Quinone Diels-Alder Reactions with 1,3,3-Trimethyl-2-vinylcyclohexenes: Regioselective Synthesis of 12-Methyl-podocarpane Diterpenes and Isolation of a Hetero Diels-Alder Product from 1,4-Benzoquinone
- 1 July 1992
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 22 (14) , 2031-2042
- https://doi.org/10.1080/00397919208021337
Abstract
Diels-Alder reactions of 2-[(E)-β-alkoxyvinyl]-1,3,3-trimethyl-cyclohexenes with 2-methoxy-3-methyl-1,4-benzoquinone regioselectively produce adducts possessing the 12-methyl-podocarpane ring skeleton. In addition, in the reaction with 1,4-benzoquinone an unusual hetero Diels-Alder product involving the C[dbnd]O group of the quinone is found in low yield.Keywords
This publication has 7 references indexed in Scilit:
- A new general synthetic approach to diterpenes: application to syntheses of (.+-.)-taxodione and (.+-.)-royleanoneThe Journal of Organic Chemistry, 1989
- Regiospecific addition of monooxygenated dienes to halo quinonesThe Journal of Organic Chemistry, 1988
- Total synthesis of amphimedineJournal of the American Chemical Society, 1988
- Proton and carbon-13 assignments from sensitivity-enhanced detection of heteronuclear multiple-bond connectivity by 2D multiple quantum NMRJournal of the American Chemical Society, 1986
- Reactions of ketene acetals 15. Regiospecific syntheses of erythrolaccin and “7-hydroxyerythrolaccin”.Tetrahedron, 1984
- The Orientation of Oxidation of 7-Hydroxy-2, 3-diphenylbenzofuran and -benzo [b]-thiophene with Fremy's Salt : The Studies on the Heterocyclic Quinones. IIYAKUGAKU ZASSHI, 1970
- 964. Organic photochemistry. Part III. The effect of light on some Diels–Alder systemsJournal of the Chemical Society, 1965