Synthesis of the marine alkaloids rhopaladins A, B, C and D

The total synthesis of all four known rhopaladins, A–D, isolated from the Okinawan marine tunicate Rhopalaea sp., in two synthetic steps is described, involving an imidate based cyclization with tryptophan esters as the key step to afford the appropriately substituted imidazolinone unit. A short and...

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Bibliographic Details
Published in:Tetrahedron 2002, Vol.58 (14), p.2813-2819
Main Authors: Janosik, Tomasz, Johnson, Ann-Louise, Bergman, Jan
Format: Article
Language:English
Subjects:
alkaloids
imidates
Medicin och hälsovetenskap
rhopaladins
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Summary:The total synthesis of all four known rhopaladins, A–D, isolated from the Okinawan marine tunicate Rhopalaea sp., in two synthetic steps is described, involving an imidate based cyclization with tryptophan esters as the key step to afford the appropriately substituted imidazolinone unit. A short and efficient new synthesis of indol-3-yl-carbonyl nitriles from indol-3-yl-carboxaldehydes and trimethylsilyl cyanide, followed by oxidation with DDQ is also described. Graphic
ISSN:0040-4020
1464-5416
1464-5416
DOI:10.1016/S0040-4020(02)00171-0