ENANTIOMERIC RELATIONSHIPS AND ANTHELMINTIC ACTIVITY OF DYSININ DERIVATIVES FROM DYSIDEA MARINE SPONGES

Dysinin-type sesquiterpenes have been isolated during an investigation of the anthelmintic constituents of Dysideaherbacea collected from Fiji. These are (—)-(6R, 1IR)-furodysinin [4], (—)-(6R, 11R)-thiofurodysinin acetate [5], (—)-(6R, 11R)-furodysinin disulfide [6], and (+)-(4S,6R, 11R)-methoxythiofurodysinin acetate lactone [7]. Experimental and molecular-mechanics-calculated1H-nmr J values provided insights about the conformation and relative stereochemistry of 7. Three of these compounds have been previously isolated as (+)-4 and (+)-5 with no absolute stereochemistry assigned and 6 (no optical properties reported). Absolute stereochemistry was assigned after establishing a chemical relationship between (—)-5, (—)-6, and(+)-7 with (—)-(6R, 11R)-furodysinin [4]. © 1990, American Chemical Society. All rights reserved.