Total synthesis of asterelin A was accomplished by applying intramolecular Suzuki-Miyaura and oxidative couplings to the formation of an 18-membered macrocyclic ring and a dibenzofuran respectively.
AsakawaY. (1995) In Progress in Chemistry of Organic Natural Product; HerzW, KirbyGW, MooreRE, SteglichW, TammC. (Eds). Springer: Vienna, 65, 618–621.
2.
AsakawaY. (1984) Phytochemisty of hepatical: Isolation of biologically active aromatic compounds and terpenoids. Revista Latinoamericana de Quimica, 14, 109–114.
3.
KodamaM, ShiobaraY, SumitomoH, MatsumuraK, TsukamotoM, HaradaC., (1988) Total syntheses of marchantin A and riccardin B, cytotoxic bis(bibenzyls) from liverworts. Journal of Organic Chemistry, 53, 72–77.
4.
HarrowvenDC, KostiukSL. (2012) Macrocyclic bisbibenzyl natural products and their chemical synthesis. Natural Product Reports, 29, 223–242.
FukuyamaY, YasoH, MoriT, TakahasiH, MinamiH, KodamaM., (2001) Total syntheses of plagiochins A and D, macrocyclic bis(bibenzyls), by Pd(0) catalyzed intramolecular Stille-Kelly reaction. Heterocycles, 54, 259–274.
7.
EsumiT, WadaM, MizushimaE, SatoN, KodamaM, AsakawaY, FukuyamaY., (2004) Efficient synthesis of isoplagiochin D, a macrocyclic bis(bibenzyls), by utilizing an intramolecular Suzuki–Miyaura reaction. Tetrahedron Letters, 45, 6941–6945.
8.
HiokiH, ShimaN, KawaguchiK, HaradaK, KuboM, EsumiT, Nishimaki-MogamiT, SawadaJ, HashimotoT, AsakawaY, FukuyamaY., (2009) Synthesis of riccardin C and its seven analogues. Part 1: The role of their phenolic hydroxyl groups as LXR α agonists. Bioorganic Medicinal Chemistry Letters, 19, 738–741.
9.
QuJ, XieC, GuoH, YuW, LouH. (2007) Antifungal dibenzofuran bis(bibenzyl)s from the liverwort Asterella angusta. Phytochemistry, 68, 1767–1774.
10.
BaileyKL, MolinskiTF. (1999) Entropically favorable macrolactamization. Synthesis of isodityrosine peptide analogues by tandem Erlenmeyer condensation-macrolactamization. The Journal of Organic Chemistry, 64, 2500–2504.
11.
AnnunziataR, FornasierR, MontanariF., (1974) Evidence for the formation of diimide in the thermal fragmentation of 1-amino-2,2-diphenylaziridine. Journal of Organic Chemistry, 39, 3195–3197;
SchwartzMA, RoseBF, HoltonRA, ScottSW, VishnuvajjalaB., (1977) Intramolecular oxidative coupling of diphenolic, monophenolic, and nonphenolic substrates. Journal of the American Chemical Society, 99, 2571–2578.
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