Iminophosphorane-mediated synthesis of 1-acyl-β-carbolines : A new access to the alkaloids eudistomin T, S and xestomanzamine A of marine origin

Article abstract of DOI:10.1016/S0040-4039(97)82962-0

New syntheses of the alkaloids eudistomin T and S are described. The key step, formation of the 1-phenylacetyl β-carboline, involves a tandem aza Wittig/electrocyclic ring closure process. The first synthesis of the alkaloid xestomanzamine A is achieved by coupling of a N-protected harmane, now available via aza Wittig/electrocyclic ring closure process, with a 5-lithioimidazole derivative.