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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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| Published in: | Tetrahedron 2019-12, Vol.75 (49), p.130714, Article 130714 |
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| Main Authors: | , , , , |
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| cites | cdi_FETCH-LOGICAL-c428t-c5c651bb50ca52e315c6ff58493484a2952f82d3655e2b9092f0436c79bc82ae3 |
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| container_issue | 49 |
| container_start_page | 130714 |
| container_title | Tetrahedron |
| container_volume | 75 |
| creator | Lambson, Katharine E. Dacko, Christopher A. McNeill, Jeffrey M. Akhmedov, Novruz G. Söderberg, Björn C.G. |
| description | 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.
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•Total syntheses and structure corroboration of dilemmaones A-B. |
| doi_str_mv | 10.1016/j.tet.2019.130714 |
| format | article |
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•Total syntheses and structure corroboration of dilemmaones A-B.</abstract><pub>Elsevier Ltd</pub><pmid>32863445</pmid><doi>10.1016/j.tet.2019.130714</doi><oa>free_for_read</oa></addata></record> |
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| source | ScienceDirect Freedom Collection |
| title | Synthesis of the tricyclic indole alkaloids, dilemmaones A and B |
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