Regio‐ and stereoselective preparation of ascomycin‐d 1  and FK 506‐d 1 | Zendy

Acemoglu Murat | Zendy; Andres Hendrik | Zendy; Moenius Thomas | Zendy

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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.

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