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Regio- and stereoselective preparation of ascomycin-d1 and FK 506-d1

✍ Scribed by Murat Acemoglu; Hendrik Andres; Thomas Moenius

Publisher
John Wiley and Sons
Year
2002
Tongue
French
Weight
123 KB
Volume
45
Category
Article
ISSN
0022-2135

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✦ Synopsis

The immunosuppressive macrolides ascomycin % 1 and FK 506 % 2 were stereoselectively deuteriated at C(32) using Curran's radical translocating method. Both AIBN and Et 3 B/O 2 were tested as radical initiator for the radical translocation/reduction step with Bu 3 SnD as reducing agent. Despite only minor structural differences, ascomycin and FK 506 showed remarkably different behaviour under the radical translocation/reduction conditions. Higher stereoselectivities were observed with Et 3 B/O 2 as initiator, presumably due to lower reaction temperatures applied in this case.

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