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Synfacts 2007(7): 0767-0767  
DOI: 10.1055/s-2007-968695
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Solid-Phase Synthesis of Oxathiocoraline

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada
J. Tulla-Puche*, N. Bayó-Puxan, J. A. Moreno, A. M. Francesch, C. Cuevas, M. Álvarez, F. Albericio*
Institute for Research in Biomedicine, Barcelona, PharmaMar, S. A. U., Madrid and University of Barcelona, Spain
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Publication History

Publication Date:
22 June 2007 (online)

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Significance

The first solid-phase total synthesis of oxathiocoraline 1, a member of the quinoxaline antibiotic family, was achieved. Thus, from Wang resin 2 and Fmoc-Gly-OH, polymer-supported 3 was synthesized in 8 steps (89% purity). The key disulfide formation (dimerization) was performed with I2 in DMF to give 4. Cleavage of the dimer from the resin with concomitant cleavage of the Boc group, subsequent bismacrolactamization followed by incorporation of the heterocyclic unit afforded oxathiocoraline 1. Crude 1 was obtained in 7% overall yield after purification by semipreparative HPLC.