Haplophytine. A Novel Type of Indole Alkaloid

Abstract

Haplophytine, the principal alkaloid of Haplophyton cimicidum, has the formula C37H40N4O7. It undergoes cleavage with acids to give aspidophytine (18) and with zinc and acid to give canthiphytine (5); the latter has been synthesized independently. Cmr spectroscopic and other studies show that haplophytine undergoes reversible skeletal rearrangement on conversion to haplophytine dihydrobromide (3). Structure 6 is proposed for haplophytine on the basis of its spectra and those of its derivatives, including tetrahydrohaplophytine-I and tetrahydrohaplophytine-II, formed by catalytic reduction and reduction with sodium borohydride, respectively. © 1973, American Chemical Society. All rights reser..