Stereocontrolled syntheses of novel styryl lactones, (+)-goniodiol, (+)-goniotriol, (+)-8-acetylgoniotriol, (+)-goniofufurone, (+)-9-deoxygoniopypyrone, (+)-goniopypyrone, and (+)-altholactone from common intermediates and cytotoxicity of their congeners

Concise syntheses of (+)-goniodiol, (+)-goniotriol, (+)-8-acetylgoniotriol, (+)-goniofufurone, (+)-9-deoxygoniopypyrone, (+)-goniopypyrone, and (+)alt holactone and their congeners from chiral lactonic aldehydes 27 and 36 as c ommon intermediates are described. The key features in the syntheses are ba sed on the in situ generation of unstable aldehydes 27 and 36 followed by t heir chemoselective reaction with triisopropoxyphenyltitanium to afford bot h diastereomers 28, 29 and 37, 38 at the C-8 positions. The cytotoxicity of styryl lactone congeners against P388 murine leukemia cells was examined. (C) 1999 Elsevier Science Ltd. All rights reserved.