A synthesis of 18-O-methyl mycalamide B

• DOI: 10.1039/p19960001797
• Publication Date: 2004-04-26T12:24:54Z
• Authors: Philip Kocienski; Piotr Raubo; Justin K. Davis; F. Thomas Boyle; Donna E. Davies; Audrey Richter
• Keywords: Dihydropyran; Derivative (finance); Amide; Methyl group

Metallated dihydropyran 9 and the dihydropyranone 10 previously used in a synthesis of insect toxin pederin were adapted to 18-O-methyl mycalamide B, most potent derivative anti-tumour agents isolated from sponge. Key steps include oxidation enol silane 11 more hindered face using dimethyldioxirane introduce hydroxy group at C-12 acylation 6-lithio-3,4-dihydro-2H-pyran with oxalamide 8 forge N-(1-alkoxy-1-alkyl)amide bridge. Biological tests human tumour cell lines confirm anti-proliferative effect B pM concentrations.