Synthesis p. 239 - 241 (1994)
Update date:2022-08-05
Topics:
Gellerman
Rudi
Kashman
A two-step biomimetic synthesis of the pentacyclic pyrido[2,3,4- kl]acridine marine alkaloid ascididemin (3a) from quinolinequinone 5a and N- trifluoroacetamidokynuramine (4) is described. The crucial step (6 to 7) involves the simultaneous formation of two pyridine rings in a process which might well offer an explanation for the biogenetic synthesis in marine organisms. The preparation of substituted ascididemins by either starting from substituted quinolinequinones, e.g., 5b to afford 11-methoxyascididemin (3b), or by nitration of 3a to the mono 1- or 3-nitroascididemins (8 and 9 respectively) is reported.
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Doi:10.1016/0040-4020(95)00201-I
(1995)Doi:10.1002/adsc.201400978
(2015)Doi:10.1016/j.tetasy.2013.12.005
(2014)Doi:10.1016/0022-328X(94)80025-1
(1994)Doi:10.1021/om00017a051
(1994)Doi:10.1016/j.ejmech.2013.11.002
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