ASYMMETRIC TOTAL SYNTHESIS OF 3S,9Z,15Z)-9,12,13-TRIHYDROXYOCTADECA-9,15-DIENOIC ACID, A SELF-DEFENSIVE AGENT AGAINST RICE-BLAST DISEASE

Authors
Citation
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
Citations number
25
Categorie Soggetti
Chemistry
Journal title
ISSN journal
0018019X
Volume
77
Issue
6
Year of publication
1994
Pages
1500 - 1504
Database
ISI
SICI code
0018-019X(1994)77:6<1500:ATSO3>2.0.ZU;2-Z
Abstract
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).