Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 2:  Synthesis of Fragments C₁_-₆ and C_9-14

Abstract

Kilogram-scale syntheses of fragments C 1 - 6 ( 6 ) and C 9 - 14 ( 4 ) of (+)-discodermolide from common precursor 3 are described. Improved procedures for each step of both fragments were developed by minimizing or eliminating the formation of byproducts that were isolated and characterized in Smith's synthesis.