Steroidal cyclobutanones, V. the baeyer-villiger rearrangement of α-substituted β-spirocyclobutanones

✍ Scribed by Paryzek, Zdzislaw ;Blaszczyk, Krzysztof

• Book ID: 102367312
• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 477 KB
• Volume: 1995
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199519950242

✦ Synopsis

Abstract

The reaction of the steroidal spiro‐α,α‐dichlorocyclobutanone 1 carried out in basic H~2~O~2~/MeOH/THF solution proceeds with cine substitution leading to the intermediate α‐chloro‐α‐methoxycyclobutanone 7 followed by the Baeyer‐Villiger rearrangement giving the spiro‐α‐chloro‐γ‐methoxylactone 9 as a mixture of four stereoisomers. The oxidation of the α‐chlorocyclobutanone 12 gives the methoxylactone 10 resulting also from a cine substitution preceding the rearrangement. The unusual transformation of 1 to the succinic anhydride derivative 14 is also observed.