TY - JOUR
T1 - Total Synthesis of Dolatrienoic Acid
T2 - A Subunit of Dolastatin 14
AU - Mouné, Sylvie
AU - Niel, Gilles
AU - Busquet, Magali
AU - Eggleston, Ian
AU - Jouin, Patrick
PY - 1997
Y1 - 1997
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=1542608053&partnerID=8YFLogxK
U2 - 10.1021/jo962217a
DO - 10.1021/jo962217a
M3 - Article
AN - SCOPUS:0030993705
SN - 0022-3263
VL - 62
SP - 3324
EP - 3331
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 10
ER -