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Studies on the Introduction of a Photoreactive Aryldiazirine Group into the Vitamin D Skeleton
Author(s) -
FernándezGacio Ana,
Mouriño Antonio
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200208)2002:15<2529::aid-ejoc2529>3.0.co;2-2
Subject(s) - chemistry , photoaffinity labeling , convergent synthesis , stereochemistry , vitamin , side chain , protecting group , organic chemistry , biochemistry , binding site , polymer , alkyl
The synthesis of a vitamin D analog with a diazirinyl benzylidene fragment replacing the side chain shows that diazirinylarylation of the upper vitamin D unit does not prevent the use of the convergent Lythgoe−Hoffman La Roche route to photoreactive analogs of potential value for photoaffinity labeling. The key step towards the diazirinylarylated upper fragment is the simultaneous oxidation of the hydroxyl and diaziridinyl groups of intermediate 10 . (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)