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Synthesis of the ABH rings of ecteinascidin 597 using a connective Pummerer-type cyclisation

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  • Chemistry

Abstract

S1 Synthesis of the ABH rings of ecteinascidin 597 using a connective Pummerer-type cyclisation Laura H. S. Smith, a Trung Thanh Nguyen, a Helen F. Sneddon, b David J. Procter* a a School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK; b Medicines Research Centre, GlaxoSmithKline, Gunnels Wood Road, Stevenage, Herts, SG1 2NY, UK Contents General experimental ............................................................................................................... S1 Synthesis of simple 4-sulfanyl tetrahydroisoquinolinones ...................................................... S2 Synthesis of model ABH ring systems .................................................................................. S12 Synthesis of the protected ABH ring system ......................................................................... S27 NMR Spectra of New Compounds ........................................................................................ S44 Chiral HPLC Chromatograms................................................................................................ S86 X-Ray Crystal Structure of 11 ............................................................................................... S89 General experimental All experiments were performed under an atmosphere of nitrogen, using anhydrous solvents, unless stated otherwise. THF was distilled from sodium and benzophenone, CH2Cl2, NEt3 and toluene were distilled from CaH2.ZnCl2 was dried in the oven at 120 °C. Microwave reactions were carried out using a Biotage Initiator. 1 H NMR and 13 C NMR were recorded using 300, 400 and 500 MHz spectrometers, with chemical shift values reported in ppm relative to residual chloroform (δH = 7.27 or δC = 77.2) or DMSO (δH = 2.50 or δC = 39.5) as internal standards. All coupling constants (J) are reported in Hertz (Hz). Mass spectra were obtained using positive and negative electr

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