Haouamines A, B, and their derivatives were synthesized via Suzuki-Miyaura coupling and three key cyclization reactions as follows: the newly developed palladium(0)-catalyzed arylativec yclizationo fp henylalaninederivedalkyne-aldehydes with 2-bromoarylboronic acid (an "anti-Wacker"-type cyclization);B F 3 •OEt 2-promoted Friedel-Crafts-type cyclization of symmetrical electron-rich aromatic rings adjacentt oatertiary allylic alcohol leading to the indeno-tetrahydropyridine skeleton;a nd (cyanomethyl)trimethylphosphonium iodide-mediated macrocyclizationo fa mino alcohols to afford aza-paracyclophane precursors. The palladium-catalyzed reductiono fm onoand di-triflate intermediates in the later stages enabled the alteration of both the position and number of hydroxyl groups on the C-ring.T he instability of haouamine B was dramatically improved by salt formation with formic acid. An unambiguous evaluation of the cytotoxicity of the prepared haouamine derivativef ormates with and withouth ydroxyl groups at different positions on the Cring indicated that the catechol structure in haouamine B produced weakcytotoxicity. Scheme1.The strategy used herein for haouamines A(1a)and B(1b)syntheses (pin = pinacolato, TBS = tert-butyldimethylsilyl).