TY - JOUR
T1 - Enantiospecific synthesis of (-)-5-epi-shikimic acid and (-)-shikimic acid
AU - Jiang, Shende
AU - McCullough, Kevin J.
AU - Mekki, Boualem
AU - Singh, Gurdial
AU - Wightman, Richard H.
PY - 1997/6/21
Y1 - 1997/6/21
N2 - Diastereoselective reaction of 2,3-O-isopropylidene-D-ribose with allylmagnesium chloride gave a 5 : 1 mixture of triols 4 and 5, which were then converted to nitrones 8 and 9. Intramolecular nitrone cycloaddition gave the isoxazolidines 10 and 11, which on acetylation gave the corresponding acetates 12 and 13 which were separated by repeated crystallisation. The major adduct 12 was converted to (-)-5-epi-shikimic acid 2. Reaction of the ribonolactone derivative 20 with allylmagnesium chloride gave the hemiacetal 21. Reduction of compound 21 with DIBAL afforded exclusively the diol 22, which was desilylated to give the triol 5. Similar chemistry to that employed for the synthesis of (-)-5-epi-shikimic acid 2 with the diol 5 resulted in the synthesis of (-)-shikimic acid 1.
AB - Diastereoselective reaction of 2,3-O-isopropylidene-D-ribose with allylmagnesium chloride gave a 5 : 1 mixture of triols 4 and 5, which were then converted to nitrones 8 and 9. Intramolecular nitrone cycloaddition gave the isoxazolidines 10 and 11, which on acetylation gave the corresponding acetates 12 and 13 which were separated by repeated crystallisation. The major adduct 12 was converted to (-)-5-epi-shikimic acid 2. Reaction of the ribonolactone derivative 20 with allylmagnesium chloride gave the hemiacetal 21. Reduction of compound 21 with DIBAL afforded exclusively the diol 22, which was desilylated to give the triol 5. Similar chemistry to that employed for the synthesis of (-)-5-epi-shikimic acid 2 with the diol 5 resulted in the synthesis of (-)-shikimic acid 1.
UR - http://www.scopus.com/inward/record.url?scp=33748585985&partnerID=8YFLogxK
U2 - 10.1002/jlcr.2580311107
DO - 10.1002/jlcr.2580311107
M3 - Article
SN - 0300-922X
VL - 12
SP - 1805
EP - 1814
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 12
ER -