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A versatile approach to the synthesis of 4,5-dioxoaporphine and 3,4-dioxocularine alkaloids. One-Pot sequential CB ring formation from arylacetamides

✍ Scribed by Rafael Suau; Juan Manuel López-Romero; Rodrigo Rico

Publisher
Elsevier Science
Year
1996
Tongue
French
Weight
230 KB
Volume
37
Category
Article
ISSN
0040-4039

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✦ Synopsis

Cyelization of biaD:lacetamides to their phenanthrene derivatives is promoted by oxalyl ehloride/stannyl chloride. The reaction proceeds with a second cyclization in which the oxalyl fragment acts as an t~-dicarlx~vI transfer agent to give 4,5-dioxoaporphine alkaloids in a single step. This double cyclization was also applied to aryloxyphenyl acetamides to give the corresponding 3,4dioxocularine alkaloids. Decarbonylated aristocularine alkaloids were also formed in this case.

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