Concise synthetic route to both enantiomeric forms of 2,3,4,4a-tetrahydro[1,3]dioxolo[4,5-j]phenanthridin-6(5H)-one, the tetracyclic skeleton associated with the narcissus alkaloids lycoricidine and narciclasine
Both enantiomeric forms, (S)-4 and (R)-4, of the tetracyclic skeleton associated with the title alkaloids 1 and 2 have been prepared; the key step involved silver isocyanate-promoted ring-opening of gem-dibromocyclopropane 5 and trapping of the resulting
Banwell,Cowden,Mackay
p. 61 - 62
(2007/10/02)
Convergent Routes to the Dioxolophenanthridin-6(5H)-one and 2,3,4,4a-Tetrahydrodioxolophenanthridin-6(5H)-one Nuclei. Application to Syntheses of the Amaryllidaceae Alkaloids Crinasiadine, N-Methylcrinasiadine and Trisphaeridine
Convergent routes to the title nuclei, (1) and (6), have been developed.Thus, Suzuki coupling of boronic acid (8) with aryl bromide (9) gave the biarylylcarbamate (7) which, on treatment with phosphorus oxychloride (POCl3), underwent Bischler-Napieralski
Banwell, Martin G.,Cowden, Cameron J.
p. 2235 - 2254
(2007/10/02)
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