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An efficient, stereoselective synthesis of (−)-bulgecinine from (S)-aspartic acid

✍ Scribed by Susanna Fehn; Klaus Burger

Publisher
Elsevier Science
Year
1997
Tongue
English
Weight
299 KB
Volume
8
Category
Article
ISSN
0957-4166

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✦ Synopsis

A stereoselective synthesis of (2S,4S,5R)-4-hydroxy-5-hydroxymethylproline 1 starting from (S)-aspartic acid 2 is described. The key step of the synthesis is the [Rh(OAc)2]2 catalyzed stereospecific transformation (de >98%) of the hexafluoroacetone protected diazoketone 5 into the 4-oxoproline derivative 7. The keto function of 7 was reduced with high diastereoselectivity (de >88%) to give the 4-cis-hydroxyproline derivative 8. After deprotection (-)-bulgecinine 1 was obtained from 9 on reduction of the ester moiety with LiBHEt3.

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