American Chemical Society
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Total Synthesis of Dolatrienoic Acid:  A Subunit of Dolastatin 14

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journal contribution
posted on 1997-05-16, 00:00 authored by Sylvie Mouné,, Gilles Niel, Magali Busquet, Ian Eggleston, Patrick Jouin
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.