Synthesis of the C1-C12 Fragment of Calyculin C

Olga V. Konstantinova; Ari M.P. Koskinen

doi:10.1055/s-0037-1610387

Synthesis of the C1-C12 Fragment of Calyculin C

Olga V. Konstantinova, Ari M.P. Koskinen^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Scientific › peer-review

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Abstract

Calyculins are a class of highly cytotoxic metabolites originally isolated from the marine sponge Discodermia calyx. To date, a total of twelve different calyculins (A-J) and calyculinamides (A, B and F) have been described, the most abundant (in D. calyx) being calyculins A and C. Herein, we demonstrate a concise route to access the C1-C12 tetraene fragment of calyculin C using transition-metal-catalyzed coupling reactions (Suzuki-Miyaura, Stille, Negishi and Heck) for the key connections. The synthesis starts from propionaldehyde and proceeds in 10 steps with 7.5% overall yield. We also describe an efficient route for the preparation of (Z)-3-iodobut-2-enenitrile in four steps and 68% yield.

Original language	English
Pages (from-to)	285-295
Number of pages	11
Journal	Synthesis (Germany)
Volume	51
Issue number	1
DOIs	https://doi.org/10.1055/s-0037-1610387
Publication status	Published - 1 Jan 2019
MoE publication type	A1 Journal article-refereed

Keywords

calyculins
natural products
Negishi and Heck coupling
Stille
Suzuki-Miyaura
syntheses of di- and polyenes
transition-metal-catalyzed cross-coupling

Access to Document

10.1055/s-0037-1610387

CHEM-Koskinen-Konstantinova-Synthesis of the C1-2019-SynthesisFinal published version, 599 KBLicence: CC BY-NC-ND

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Konstantinova, O. V., & Koskinen, A. M. P. (2019). Synthesis of the C1-C12 Fragment of Calyculin C. Synthesis (Germany), 51(1), 285-295. https://doi.org/10.1055/s-0037-1610387

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