Product derivatization. Conditions. (i) Conversion of 20 to form 34: Pd/C (10 mol%), H 2 , MeOH (0.1 M), r.t., 24 h. (ii) Semi-reduction to generate the Z -alkene 35 : TiCl 2 Cp 2 (10 mol%), LiAlH 4 (2.0 equiv.), tetrahydrofuran (THF) (0.2 M), r.t., overnight. (iii) Generation of quinoxaline 36 : (1) RuCl 3 (1 mol%), PhI(OAc) 2 (3.0 equiv.), DCM, H 2 O (4:1, 0.2 M), r.t., 3 h; (2) saccharin (5 mol%), 1,2-phenylendiamine (1.1 equiv.), MeOH (0.2 M), r.t., 12 h. (iv) TIPS deprotection to generate terminal alkyne 37 : TBAF (2.0 equiv.), THF (0.4 M), r.t., 2 h. (v) Formation of triazole 38 via a copper-catalysed click reaction: CuTc (10 mol%), 4-acetamidobenzenesulfonyl azide (1.2 equiv.), toluene (0.2 M), r.t., 12 h. (vi) In situ deprotection of 33 and subsequent Sonogashira cross-coupling: Pd(PPh 3 ) 2 Cl 2 (4.5 mol%), CuI (5 mol%), 4-iodoanisole (1.2 equiv.), NEt 3 (7.0 equiv.), TBAF (2.0 equiv.), THF (0.2 M), 45 C, 12 h. (vii) Suzuki-coupling to generate compound 40 : Pd(PPh 3 ) 4 (10 mol%), 2-furanboronic acid (2.5 equiv.), K 2 CO 3 (2.5 equiv., 2 M in H 2 O), dimethoxyethane (DME) (0.2 M), 85 C, overnight.
