Antiproliferating Polyquinanes. VI. : Synthesis of 2-Methylene[3.3.3]propellan-3-one Derivatives with Hydrophilic Groups

Abstract

New analogues related to 2-methylenetricyclo[3.3.3.0]undecan-3-one (4), which shows potent antiproliferating activity, i.e., 2-(methoxymethoxy)-4-methylenetricyclo[3.3.3.0]undecan-3-one (5), (1S^*, 5R^*, 7S^*)-7-(methoxymethoxy)- and hydroxy-2-methylenetricyclo[3.3.3.0]undecan-3-ones (6 and 7), and (1S^*, 5R^*, 8S^*)-8-(methoxymethoxy)- and hydroxy-2-methylenetricyclo[3.3.3.0]-undecan-3-ones (8 and 9), were readily synthesized through skeletal transformations of derivatives of tricyclo[4.3.2.0]undecan-2-one (2).