Total Synthesis of Apoptolidin: Completion of the Synthesis and Analogue Synthesis and Evaluation Academic Article uri icon

Overview

MeSH Major

  • Macrolides

abstract

  • The total synthesis of apoptolidin (1) is reported together with the design, synthesis, and biological evaluation of a number of analogues. The assembly of key fragments 6 and 7 to vinyl iodide 3 via dithiane coupling technology was supplemented by a second generation route to this advanced intermediate involving a Horner-Wadsworth-Emmons coupling of fragments 22 and 25. The final stages of the synthesis featured a Stille coupling between vinyl iodide 3 and vinylstannane 2, a Yamaguchi lactonization, a number of glycosidations, and final deprotection. The developed synthetic technology was applied to the construction of several analogues including 74, 75, and 77 which exhibit significant bioactivity against tumor cells.

publication date

  • December 17, 2003

Research

keywords

  • Academic Article

Identity

Language

  • eng

Digital Object Identifier (DOI)

  • 10.1021/ja030496v

PubMed ID

  • 14664590

Additional Document Info

start page

  • 15443

end page

  • 54

volume

  • 125

number

  • 50