Synthesis of the tricyclic indole alkaloids, dilemmaones A and B

Dilemmaones A-C are naturally occurring tricyclic indole alkaloids possessing a unique hydroxymethylene or methoxymethylene substituent at the C2 position of the indole core and a C6–C7 fused cyclopentanone. Dilemmaone B has been prepared in 5 steps from 5-methylindan-1-one, and dilemmaone A has bee...

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Bibliographic Details
Published in:Tetrahedron 2019-12, Vol.75 (49), p.130714, Article 130714
Main Authors: Lambson, Katharine E., Dacko, Christopher A., McNeill, Jeffrey M., Akhmedov, Novruz G., Söderberg, Björn C.G.
Format: Article
Language:English
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Summary:Dilemmaones A-C are naturally occurring tricyclic indole alkaloids possessing a unique hydroxymethylene or methoxymethylene substituent at the C2 position of the indole core and a C6–C7 fused cyclopentanone. Dilemmaone B has been prepared in 5 steps from 5-methylindan-1-one, and dilemmaone A has been prepared in 3 steps from a common precursor, 6-bromo-5-methyl-7-nitroindan-1-one. In both syntheses, key steps include a Kosugi-Migita-Stille cross coupling and a reductive cyclization using hydrogen gas and a transition metal catalyst. [Display omitted] •Total syntheses and structure corroboration of dilemmaones A-B.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2019.130714