RYANOIDS AND RELATED-COMPOUNDS - IDENTIFICATION OF 5 NEW RYANOIDS FROM THE PLANT RYANIA-SPECIOSA VAHL - FORMAL TOTAL SYNTHESES OF 3-DEOXYRYANODOL (CINNZEYLANOL), 10-O-ACETYL-3-DEOXYRYANODOL (CINNZEYLANINE), 2-DEOXYRYANODOL, 2-DEOXY-2-EPIRYANODOL, 2,3-DIDEOXY-2,3-DIHYDRORYANODOL,2-DEOXY-3-EPIRYANODOL, AND 2-DEOXY-3-EPIRYANODINE

In the course of a preliminary investigation on the relationships betw een the chemical structure of ryanoids and their affinity to the ryano dine binding site, we have isolated, from the plant Ryania speciosa Va hl, four new members of this family of natural insecticidal compounds (ryanoids 3, 4, 5, and 6) and corrected the reported structure of a fi fth one (ryanoid 7). In addition, we have synthesized, from anhydrorya nodol (10), new members of this family having fewer hydroxyl groups in ring A: cinnzeylanol (14) and cinnzeylanine (15), 2,3-dideoxy-2,3-dih ydroryanodol (16), 2-deoxy-3-epiryanodol (18), and 2-deoxy-3-epiryanod ine (19), 2-deoxyryanodol (20), and 2-deoxy-2-epiryanodol (21).