- Chiral pool synthesis of calystegine A3 from 2-deoxyglucose via a Brown allylation
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Calystegine A3 is a naturally occurring nortropane iminosugar of which there previously have been three total syntheses. Inspired by our previous work we here report on a fourth approach using 17 steps from 2-deoxy-d-glucose applying a diastereoselective allylation protocol.
- Rasmussen, Tina Secher,Jensen, Henrik Helligs?
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experimental part
p. 2855 - 2861
(2012/01/04)
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- Synthesis of calystegine A3 from glucose by the use of ring-closing metathesis
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A synthesis of the nortropane alkaloid calystegine A3 is described from D-glucose. The key step employs a zinc-mediated tandem reaction where a benzyl-protected methyl 6iodo glucoside is fragmented to give an unsaturated aldehyde, which is then transformed into the corresponding benzylimine and allylated in the same pot. The functionalized nona-l,8-diene, thus obtained, is converted into the sevenmembered carbon skeleton in calystegine A3 by ring-closing olefin metathesis. Subsequent deoxygenation by the BartonMcCombie protocol, hydroboration and oxidative workup followed by hydrogenolysis affords calystegine A3. The synthesis uses a total of 13 steps from glucose and confirms the absolute configuration of the natural product.
- Monrad, Rune Nygaard,Pipper, Charlotte Bressen,Madsen, Robert
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experimental part
p. 3387 - 3395
(2011/02/28)
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