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Regio‐ and stereoselective preparation of ascomycin‐d 1 and FK 506‐d 1
Author(s) -
Acemoglu Murat,
Andres Hendrik,
Moenius Thomas
Publication year - 2002
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.558
Subject(s) - chemistry , stereoselectivity , curran , stereochemistry , radical initiator , regioselectivity , medicinal chemistry , organic chemistry , catalysis , monomer , botany , polymer , biology
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. Copyright © 2002 John Wiley & Sons, Ltd.