A. Baudat et P. Vogel, ASYMMETRIC TOTAL SYNTHESIS OF 3S,9Z,15Z)-9,12,13-TRIHYDROXYOCTADECA-9,15-DIENOIC ACID, A SELF-DEFENSIVE AGENT AGAINST RICE-BLAST DISEASE, Helvetica Chimica Acta, 77(6), 1994, pp. 1500-1504
The Diels-Alder adduct of furan and 1-cyanovinyl (1'R)-camphanate was
converted into methyl[(tert-butyl)dimethylsilyl O-isopropylidene-beta-
L-ribo-hexofuranosid]uronate ((+)-4). Reduction with diisobutylalumini
um hydride gave the corresponding aldehyde which was condensed with th
e ylide derived from triphenyl(propyl)phosphonium bromide to give ,3-(
isopropylidenedioxy)-4-[(Z)-pent-2'-enyl]furan ((+)-7). Removal of the
silyl protective group gave a mixture of the corresponding furanose t
hat underwent Wittig reaction with the ylide derived from [8-(methoxyc
arbonyl)octyl]triphenylphosphonium bromide to yield methyl -11,12-(iso
propylidenedioxy)octadeca-9,15-dienoate ((-)-9). Acidic hydrolysis, th
en saponification afforded 11R,12S,13S,9Z,15Z)-11,12,13-trihydroxyocta
deca-9, 15-dienoic acid (1).