Synthetic Studies Directed Toward the Marine Derived Amphidinol Natural Products C(5)-C(14), C(56), and C(57) Segments of AM7

Amphidinol 1, a bioactive compound, was isolated from a dinoflagellate in 1991. The compound (AM1) shows greater antifungal activity against Aspergillus niger than the pharmaceutical agent amphotericin B and also exhibits hemolytic activity. Other compounds in the amphidinol series exhibit these activities while the amphidinols increase cellular permeability. It was found that AM3 didn\u27t destroy the cell membrane. The atom connectivity of the AMs have been published by several groups. However, AM3 is the only member, which was fully identified in terms of relative stereochemistry and absolute configuration. Interestingly, the structurally similar luteophanols do not show bioactivity against the fungus. The unique structure of AMs consist of polyhydroxyl groups, two tetrahydropyan rings and a conjugated triene. Recently, amphidinol 7 (AM&) has been isolated and studied. This compound shows less bioactivity for Aspergillus niger compared to AM3. The polyene side chain and two oxane rings present in AM7 are also contained in other AMs, howere AM7 has a shorter polyol side chain than AM3. The relative sterochemistry of this polyol segment of AM7 has not determined. Model compounds will be prepared to elucidate the structure of the polyol chain