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A Stereoselective Formal Synthesis of (-)-Fumagillol.

✍ Scribed by Olivier Bedel; Arnaud Haudrechy; Yves Langlois


Publisher
John Wiley and Sons
Year
2005
Weight
9 KB
Volume
36
Category
Article
ISSN
0931-7597

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πŸ“œ SIMILAR VOLUMES


A Stereoselective Formal Synthesis of (βˆ’
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## Abstract A novel formal synthesis of fumagillol, a direct precursor of the antiangiogenic sesquiterpene fumagillin, is described. The main features of the synthesis are a stereoselective Claisenβˆ’Ireland rearrangement, a ring‐closing metathesis, a chemo‐ and stereoselective dihydroxylation, and a

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A 13-step synthesis of (Β±)-fumagillol (1), the direct precursor of the potent angiogenesis inhibitors TNP-470 and fumagillin, from crotonaldehyde, diethylamine, and acrolein (see the scheme) has been achieved. The synthesis features a remarkable hetero-Claisen rearrangement. Small-molecule inhibitor

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