Synthetic studies on the pederin family of antitumour agents. Syntheses of mycalamide B, theopederin D and pederin

Article abstract of DOI:10.1039/a909898d

The synthesis of mycalamide B, theopederin D and pederin, which are antitumour agents was discussed. All three compounds were prepared from 6-lithio-2,3-dimethyl-4-phenylselenomethyl-3,4-dihydro-2H-pyran and 2-(3-chloropropyl)-3,3-dimethyl-3,4-dihydro-2H-pyran-4-one. Ground state conformational models were proposed to explain the stereoselectivity of the reactions. The absolute and relative stereochemistry of the compounds has been established by X-ray crystallography and NMR studies.