SYNTHESES OF POTENTIAL SPIN PROBES FOR BIOMEMBRANES - TEMPO AND PROXYL NITROXIDES OF LITHOCHOLIC ACID

The synthesis of a steroidal spin label 10 containing a tempo nitroxide group in the side chain of lithocholic acid 1 is reported. This is the first report of a tempo nitroxide in d steroidal side chain. The methodology involved d Wittig condensation between the steroidal phosphonium ylide 7 and tem...

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Bibliographic Details
Published inTetrahedron Vol. 48; no. 45; pp. 9939 - 9950
Main Authors BANERJEE, S, TRIVEDI, GK
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 1992
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:The synthesis of a steroidal spin label 10 containing a tempo nitroxide group in the side chain of lithocholic acid 1 is reported. This is the first report of a tempo nitroxide in d steroidal side chain. The methodology involved d Wittig condensation between the steroidal phosphonium ylide 7 and tempone 9. The synthesis Of d proxyl nitroxide 16 with the proxyl group in the side chain of 1 is also described. A mild oxidation of 16 to the corresponding 3-keto spin label 17 in high yield is also achieved.
ISSN:0040-4020
DOI:10.1016/S0040-4020(01)92284-7