Total Synthesis of Dolatrienoic Acid: A Subunit of Dolastatin 14.
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.
Mouné
Sylvie
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UPR 9023, Mécanismes Moléculaires des Communications Cellulaires 141, rue de la Cardonille, 34094 Montpellier Cedex 5, France.
Niel
Gilles
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Busquet
Magali
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Eggleston
Ian
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Jouin
Patrick
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