Synthesis of the RingD-Building Block of (24S)-24-Hydroxy Vitamin D3 from Menthol, I

✍ Scribed by Daniewski, Andrzej Robert ;Warchol, Tadeusz

• Publisher: John Wiley and Sons
• Year: 1992
• Tongue: English
• Weight: 981 KB
• Volume: 1992
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.1992199201159

✦ Synopsis

Abstract

Natural (—)‐menthol (4) was oxidized to the lactone 9 which was alkylated with allyl bromide to a single product 10. The latter compound was transformed into bromo epoxide 33 which was cyclized with the highly reactive copper to the desired ring D Building block 18 of (24__S__)‐24‐hydroxy vitamin D~3~. The title compound 18 was synthesized also by free‐radical cyclization of enaldehyde 40.