Novel aspects of the ferrier carbocyclic ring-transformation reaction

✍ Scribed by Pál László; István F. Pelyvás; Ferenc Sztaricskai; László Szilágyi; Árpád Somogyi

• Publisher: Elsevier Science
• Year: 1988
• Tongue: English
• Weight: 913 KB
• Volume: 175
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(88)84145-4

✦ Synopsis

The mercury salt-mediated carbocyclic ring-transformation reaction of the 3-azido (4), 3-benzamido (S), and 3-trifluoroacetamido (11) derivatives of methyl 4-0-benzoyl-2,3,6-trideoxy-P-D-erythro-hex-5-enopyranoside, methyl 3-azido-4-0benzoyl-2,3,6-trideoxy-cu-r>-threo-hex-5-enopyranoside ( 16), and its 3-0-benzoyl-P-(14) and 3-deoxy-a-(18) analogues has been investigated. The resulting cyclohexanone derivatives 20-23, together with all of the "Ferrier-ketones", have the newly generated HO-S and the 3-substituent trans. The role of the mercury atom in exerting stereocontrol has been substantiated through the formation of the C-5 diastereoisomeric cyclohexanones 24a and 24b in the Ferrier-reaction of 18, which has no 3-substituent.

*Dedicated to Professor RezsB Bogmir in the year of his 75th birthday.