Design and synthesis of 1α,25-dihydroxyvitamin D3 analogues with fixed torsion angle C(16-17-20-22)

✍ Scribed by JoséAntonio Martínez-Pérez; Luis Sarandeses; Juan Granja; JoséAntonio Palenzuela; Antonio Mouriño

• Book ID: 104259406
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 221 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)00867-3

✦ Synopsis

A series of semi-rigid analogues of the hormone 1 ot,25-dihydroxyvitamin D3 have been designed in order to study the topology required for binding to the hormone receptor (VDR). The new vitamin D3 analogues 2-5 possess a rigid C17--C20 bond and minimal structural modifications on the side-chain with respect to the hormone. Key steps for the introduction of the side-chains of the new analogues 2-5 from hydrindanone 6 involve a stereoselective Wittig reaction, olefin isomerization and dihalocyclopropanation.