Total Synthesis and Stereochemical Reassignment of (+)-Dolastatin 19

Ian Paterson, Alison D. Findlay, Gordon John Florence

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)

Abstract

A revised configurational assignment for the cytotoxic marine macrolide dolastatin 19 is proposed and validated by total synthesis. Key features of the route include an asymmetric vinylogous aldol reaction to install the isolated C13 stereocenter and (E)-trisubstituted alkene, two sequential 1,4-syn boron-mediated aldol reactions, and a Mukaiyama glycosylation to append the L-rhamnose-derived pyranoside.

Original languageEnglish
Pages (from-to)2131-2134
Number of pages4
JournalOrganic Letters
Volume8
Issue number10
DOIs
Publication statusPublished - 11 May 2006

Keywords

  • MARINE NATURAL-PRODUCTS
  • HARE DOLABELLA-AURICULARIA
  • MACROLIDE
  • CALLIPELTOSIDE

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