ORGN 727 |
| Chitin synthase is implicated in the biogenesis of chitin. Compounds that inhibit chitin synthase have been shown to act against both insects and fungi; therefore they are of great agrochemical significance. This poster describes the synthesis of allosamizoline (4) and its future transformation into allosamidin (5). The key intermediate in our synthesis, cyclopentene (2) was prepared in multigram scale from glucosamine hydrochloride (1) in 8 steps. Iodo-mediated cyclisation of cyclopentene (2) afforded the oxazoline intermediate (3). Keck allyl addition, double bond isomerization followed by reductive ozonolysis and deprotection gave allosamizoline (4), in a total of 13 steps. Protected allosamizoline will be coupled with a ready prepared dissacharide, to obtain allosamidin (5) after global deprotection.
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Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
