Synthesis of Terpenoids. II. A New Total Synthesis of β-Cuparenone
- 1 January 1976
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 6 (1) , 11-16
- https://doi.org/10.1080/00397917608062126
Abstract
The vicinal dicuaternary arrangement, typical of cuparenetype sesquiterpenoids2, has been constructed in a variety of ways3. In this paper we describe an alternate solution to this problem exemplified in a new total synthesis of β-cuparenone 1, which involves an application of the recently introduced Stork “protected” cyanohydrin reagents4,5.Keywords
This publication has 10 references indexed in Scilit:
- Stereospecific synthesis of dl-juvabioneJournal of the American Chemical Society, 1974
- A New Approach to the Synthesis of (±)-CupareneSynthesis, 1974
- Empirical rules for estimating the reduction potential of .alpha.,.beta.-unsaturated carbonyl compoundsJournal of the American Chemical Society, 1972
- Anions of protected cyanohydrins as acyl carbanion equivalents and their use in a new synthesis of ketonesJournal of the American Chemical Society, 1971
- Steric and electronic factors in the reductive cleavage of methyl-substituted phenylcyclopropanes and spiro[2.4]hepta-4,6-dienesJournal of the American Chemical Society, 1969
- A simple synthesis of β-cuparenone and related sesquiterpenoidsJournal of the Chemical Society D: Chemical Communications, 1969
- Ketones from “mayur pankhi” : some new cuparene-based sesquiterpenoidsTetrahedron Letters, 1964
- Cuparene and cupreneneTetrahedron Letters, 1960
- THE ANOMALOUS INFRARED SPECTRA OF SOME CYCLOPENTENONESJournal of the American Chemical Society, 1958
- 516. Tropolones. Part IX. 2 : 3-Dihydro-2 : 3-methylene-1 : 4-naphthaquinoneJournal of the Chemical Society, 1956