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An efficient stereoselective synthesis of (2S,4S,5R)-(−)-bulgecinine

✍ Scribed by Antoni Krasiński; Janusz Jurczak

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
84 KB
Volume
42
Category
Article
ISSN
0040-4039

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An efficient stereoselective synthesis o
An efficient stereoselective synthesis of Z-(2S)- and Z-(2R)-2-tert-butoxycarbonylamino-6-hydroxyhex-4-enoic acid, key intermediates in the synthesis of (2S,4S,5R)-(−)- and (2R,4R,5S)-(+)-bulgecinine
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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 deriv