Implication and improvement of stereoselective methylenation of a chiral aldehyde related to total synthesis of the furaquinocins

Article abstract of DOI:10.1016/S0040-4039(97)00746-6

In relation to the total synthesis of the furaquinocins, stereoselective methylenation of chiral aldehyde 5 is described. The diastereoselectivity of epoxides 6a/b is high when stabilized sulfur ylides are employed. A double stereo-differentiation phenomenon was observed for the aminosulfoxonium ylide 8: the selectivity with (S)-8 was 30:1, while 5:1 with (R)-8.