Two homoallyl/cyclopropylalkyl rearrangements accompanying a Wolff–Kishner type reduction

✍ Scribed by Manfred Schlosser; Armin Zellner

• Book ID: 104231188
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 77 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01127-3

✦ Synopsis

Conceived as a model study for the enantioselective synthesis of the natural product (S)-bakuchiol, the deoxygenation of a recently described trishomoallyl alcohol was attempted using the Kabalka modification of the Wolff-Kishner method after prior oxidation of the alcohol to the ketone. However, an unprecedented succession of homoallyl/cyclopropyl ring closure and ring opening altered the carbon skeleton profoundly. The crucial intermediates are assumed to be radicals although carbanions cannot yet be definitely ruled out.