Synthesis ofrac-Midpacamide and thespiro-Cyclization of Its Precursor
✍ Scribed by Lindel, Thomas ;Hoffmann, Holger
- Publisher
- John Wiley and Sons
- Year
- 1997
- Tongue
- English
- Weight
- 488 KB
- Volume
- 1997
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
The alkylidene hydantoin 8 was synthesized as an analogue of the marine natural product oroidin (1) by employing a Horner‐Wadsworth‐Emmons reaction. Treatment of 8 with bromine in acetic acid induced a biomimetic spiro‐cyclization forming the ACD ring system of dibromophakellin (2) in one step. rac‐Midpacamide (10) was obtained from the same precursor through a chemoselective, ruthenium‐catalyzed hydrogenation leaving the brominated pyrrole moiety intact.
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