Total synthesis and stereochemical reassignment of (+)-dolastatin 19, a cytotoxic marine macrolide isolated from Dolabella auricularia

I Paterson, A D Findlay, Gordon John Florence

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

Using conformational analysis and biogenetic considerations, a revised configurational assignment for the cytotoxic marine macrolide dolastatin 19 is proposed, together with its validation by completion of the first total synthesis. Key features of the highly stereo-controlled route include an asymmetric vinylogous Mukaiyama aldol reaction to simultaneously install both the remote C13 stereocenter and the C10-C11 (E)-trisubstituted olefin, two sequential 1,4-syn boron-mediated aldol reactions, and a late-stage, alpha-selective Mukaiyama glycosylation to append the L-rhamnose-derived pyranoside. (C) 2007 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)5806-5819
Number of pages14
JournalTetrahedron
Volume63
Issue number26
DOIs
Publication statusPublished - 25 Jun 2007

Keywords

  • macrolide
  • cytotoxic
  • conformational analysis
  • stereochemical reassignment
  • aldol reaction
  • glycosylation
  • NATURAL-PRODUCTS
  • MOLECULAR MECHANICS
  • CHEMICAL DEFENSES
  • ALDOL REACTIONS
  • AURISIDE-A
  • CALLIPELTOSIDE
  • KETONES
  • GLYCOSIDES
  • OXIDATION
  • ALDEHYDES

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