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Synlett 1993; 1993(8): 551-552
DOI: 10.1055/s-1993-22524
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A Model Study on the Synthesis of the Marine Hepatotoxin Cylindrospermopsin

Geoffrey R. Heintzelman* , Masood Parvez, Steven M. Weinreb
  • *Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA
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Publication Date:
19 March 2002 (online)

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Model diene urea 7 has been converted to the corresponding N-sulfinyl urea 11, which undergoes stereoselective intramolecular hetero [4+2]-cycloaddition to afford dihydrothiazine oxide adduct 12. Treatment of 12 with PhMgBr, followed by stereospecific [2,3]-sigmatropic rearrangement, yields 14 which has the AB ring system and C-7,8 and 10 configuration of cyclindrospermopsin (1).