New 2-substituted functionalized allyl halides in the synthesis of fragments of amphidinolides B, D, G, H, and L

Abstract

Simple and efficient asymmetric syntheses of several new allyl bromides as C⁹–C¹⁴ fragments of cytotoxic macrolactones, amphidinolides B, D, G, H, and L, have been developed starting from accessible 1-[(2S)-4,4-dimethoxy-2-methylbutyl]cyclopropyl methanesulfonate prepared through cyclopropanol intermediates. Original synthetic approaches to the C⁷–C¹⁶, C⁷–C¹⁴, and C⁹–C¹⁶ amphidinolide fragments are also described.