Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 11, Pages 3843-3846Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo1005284
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Funding
- Ministry of Education, Culture, Sports, Science and Technology of Japan
- National Institute of Biomedical Innovation (NIBIO)
- Japan Society for the Promotion of Science (JSPS) for Young Scientists
- Grants-in-Aid for Scientific Research [22590005] Funding Source: KAKEN
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A divergent short synthesis of four diastereomers of pachastrissamine was achieved. Natural pachastrissamine was synthesized through bis-tosylation of the common intermediate and cyclization. 2-epi-Pachastrissamine was obtained by monotosylation and spontaneous cyclization of D-ribo-phytosphingosine derivative. By use of regio- and stereospecific ring-opening reaction of the orthoester assisted by a Bee group as a key step, 3-epi- and 2,3-epi-pachastrissamines were synthesized. The three stereogenic centers of all the diastereomers were constructed by using Garner's aldehyde as the sole chiral source.
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