182054-91-7Relevant academic research and scientific papers
Total synthesis of scopine, pseudoscopine, and nor-derivatives
Justice, David E.,Malpass, John R.
, p. 11977 - 11994 (1996)
Scopine and pseudoscopine have been synthesised from cyclohepta-3,5-dienol; the initial 1,4-functionalisation of the diene is based on a nitroso- cycloaddition. The use of the N-benzyloxycarbonyl group throughout the scheme allows ultimate reductive deprotection to yield N-methyl or novel NH (nor-) derivatives without damage to the exo-epoxide of the title compounds. Preliminary investigation of nitroso- cycloaddition to 5,6-epoxycyclohepta-1,3-diene is described.
Exo- and Endo-6-Hydroxy- and 6,7-Epoxytropanes; Total Synthesis of Scopine, Pseudoscopine, and Nor- Derivatives
Justice, David E.,Malpass, John R.
, p. 4689 - 4692 (2007/10/02)
Novel endo- 6,7-epoxy-8-azabicyclooctane derivatives and the corresponding exo-analogues have been synthesised and show substantially different reactivity; the resistance of the exo-epoxides to ring opening during hydride reduction and catalytic hydrogenolysis is exploited in a total synthesis of scopine, pseudoscopine, and nor- derivatives.
