Journal
JOURNAL OF ANTIBIOTICS
Volume 69, Issue 4, Pages 273-279Publisher
JAPAN ANTIBIOTICS RESEARCH ASSOC
DOI: 10.1038/ja.2016.6
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Funding
- Japan Society for the Promotion of Science (JSPS) [26288018]
- Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT)
- Grants-in-Aid for Scientific Research [26288018, 15K05436] Funding Source: KAKEN
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The practical synthesis of the C-ring precursor of paclitaxel starting from 3-methoxytoluene is described. Lipase-catalyzed kinetic resolution of a substituted cyclohexane-1,2-diol, derived from 3-methoxytoluene in three steps, successfully afforded a desired enantiomer with >99% ee, which was transformed to a cyclohexenone. 1,4-Addition of a vinyl metal species, followed by Mukaiyama aldol reaction with formalin in the presence of a Lewis acid provided the known C-ring precursor of paclitaxel in a 10 g scale.
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