Total Synthesis of Dolatrienoic Acid: A Subunit of Dolastatin 14

Sylvie Mouné, Gilles Niel, Magali Busquet, Ian Eggleston, Patrick Jouin

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31 Citations (SciVal)


The (7R,15R)- and (7S,15R)-diastereomers of dolatrienoic acid were synthesized using a convergent strategy. Fragment C5-C9 was obtained through enantiodifferentiation of racemic pentane-1,3,5-triol as the key step, fixing the chirality at C7 of fragments 4 and ent-4. The chirality at C15 of the fragment C10-C16 was introduced from L-glutamic acid. Coupling of these two fragments led to the aldehydes (7R,15R)- and (7S,15R)-2 which were homologated by Horner-Wadsworth-Emmons condensation to give (7R,15R)- and (7S,15R)-dolatrienoic acids.

Original languageEnglish
Pages (from-to)3324-3331
Number of pages8
JournalJournal of Organic Chemistry
Issue number10
Publication statusPublished - 1997

ASJC Scopus subject areas

  • Organic Chemistry


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