TY - JOUR AU - Konstantinova, Olga V.; Koskinen, Ari M.P. TI - Synthesis of the C1–C12 Fragment of Calyculin C SN - 0039-7881 SN - 1437-210X PY - 2019 JO - Synthesis JF - Synthesis LA - EN VL - 51 IS - 01 SP - 285 EP - 295 ET - 2018/11/22 DA - 2018/12/13 KW - calyculins KW - natural products KW - transition-metal-catalyzed cross-coupling KW - Suzuki–Miyaura KW - Stille KW - Negishi and Heck coupling KW - syntheses of di- and polyenes AB - 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. PB - Georg Thieme Verlag DO - 10.1055/s-0037-1610387 UR - http://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0037-1610387 ER -