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A Practical Synthesis of 14‐ epi ‐19‐ nor ‐1α,25‐Dihydroxyvitamin D 3 Analogues and Their A‐ring Epimers
Author(s) -
Wu Yusheng,
Zhao Yurui,
Tian Honjian,
Clercq Pierre De,
Vandewalle Maurits,
Berthier Marielle,
Pellegrino Gills,
Maillos Philippe,
Pascal JeanClaude
Publication year - 2001
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(200110)2001:20<3779::aid-ejoc3779>3.0.co;2-q
Subject(s) - chemistry , diastereomer , epimer , stereochemistry , ring (chemistry) , hexane , organic chemistry
A practical synthesis of (2 S ,3a S ,4a S )‐2‐ tert ‐butyldimethylsilyloxybicyclo[3.1.0]hexane‐3a‐carbaldehyde ( 14a ) and diastereoisomers, starting from all ‐ cis methyl 3,5‐dihydroxy‐1cyclohexanecarboxylate ( 24 ) is described. Coupling with appropriate cis ‐hydrindanes produces the title compounds. TX 522, a member of this series, is currently in phase II clinical studies for the treatment of psoriasis. The key step involves the coupling of 14 and 16 with the respective cis ‐hydrindanes 9 and 7 .