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

Conceived as a model study for the enantioselective synthesis of the natural product (S)-bakuchiol, the deoxygenation of a recently described trishomoallyl alc. was attempted using the Kabalka modification of the Wolff-Kishner method after prior oxidn. of the alc. 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. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 42, 34, 5863-5865
Year:
2001
Keywords:
Note:
CAN 135:331212
25-2
Benzene, Its Derivatives, and Condensed Benzenoid Compounds
Section de Chimie de l'Universite (BCh),Lausanne,Switz.
Journal
0040-4039
written in English.
357979-06-7; 369365-08-2 Role: RCT (Reactant), RACT (Reactant or reagent) (homoallyl/cyclopropylalkyl rearrangements accompanying a Wolff-Kishner type redn.); 369365-10-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (homoallyl/cyclopropylalkyl rearrangements accompanying a Wolff-Kishner type redn.); 369365-09-3P Role: SPN (Synthetic preparation), PREP (Preparation) (homoallyl/cyclopropylalkyl rearrangements accompanying a Wolff-Kishner type redn.)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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