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A simple and practical approach to the synthesis of the marine sponge pigment fascaplysin and related compounds

✍ Scribed by Oleg S. Radchenko; Vyacheslav L. Novikov; George B. Elyakov

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
190 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

Fascaplysin 1, an antimicrobial and cytotoxic red pigment of the marine sponge Fascaplysinopsis sp.. has been synthesized in five steps from tryptamine 2 in 44% overall yield. The key steps in the synthesis are: (a) dehydrogenation of the dihydro-13-.carboline intermediate 4 simultaneously with its benzylic oxidation on treatment with MnO2 and (b) the thermal cyclization of the resulting [3carboline _7 into a quaternary salt _8. Similarly, indoloisoquinolines 15 and 16, the tetracyclic analogues ofl, were prepared in six steps from ~x-amino ketone _9 in 59 and 55% overall yields, respectively.

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