Divergent Synthesis of Cytotoxic Styryl Lactones Related to Goniobutenolides A and B, and to Crassalactone D

• Published in: Organic letters Vol. 14; no. 23; pp. 5956 - 5959
• Main Authors: Popsavin, Velimir, Kovačević, Ivana, Benedeković, Goran, Popsavin, Mirjana, Kojić, Vesna, Bogdanović, Gordana
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 07.12.2012; Amer Chemical Soc
• Subjects: Annonaceae - chemistry; Antineoplastic Agents, Phytogenic - chemical synthesis; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - pharmacology; Chemistry; Chemistry, Organic; Drug Screening Assays, Antitumor; Furans - chemical synthesis; Furans - chemistry; Furans - pharmacology; Glucose - chemistry; HL-60 Cells; Humans; K562 Cells; Lactones - chemical synthesis; Lactones - chemistry; Lactones - pharmacology; Molecular Structure; Physical Sciences; Science & Technology; Spiro Compounds - chemical synthesis; Spiro Compounds - chemistry; Spiro Compounds - pharmacology; Stereoisomerism; ANTIPROLIFERATIVE ACTIVITY; (+)-GONIOFUFURONE; STYRYLLACTONES; 7-EPI-GONIOFUFURONE; UNSATURATED ESTERS
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol302860z

Goniobutenolides A (1) and B (2), crassalactone D (3), 4-epi-crassalactone D (4), and the corresponding 7-epimers have been synthesized starting from d-glucose. The key step in the synthesis of 1 and 2 is a new one-pot sequence comprised of a Z-selective Wittig olefination/lactonization/β-elimination. Preparation of 3 and 4 included the final 5-endo-trig spirocyclization of 1 and 2. The synthesized products were evaluated for their in vitro antiproliferative activity against selected tumor cell lines.