Reactivity and synthetic applications of a new synthon for substituted divinyl ketones, namely 4-[(4’-methylphenyl)sulfonyl]-1-(triphenylphosphoranylidene)-2-butanone, are reviewed. The title compound has been conveniently used in “tandem” reactions allowing for the construction of six-membered hetero- and carbocyclic rings, either in homogeneous-phase or solid-phase. Moreover, generation of its alpha-sulfonyl anion offered an easy access to multifunctionalized linear carbon frameworks. The compounds obtained through the use of 4-[(4’-methylphenyl)sulfonyl]-1-(triphenylphosphoranylidene)-2-butanone represented convenient precursors for the synthesis of several natural products, such as (±)-epibatidine, (-)-anabasine, (±)-pyrenophorin and carbacephams.
4-[(4’-Methylphenyl)sulfonyl]-1-(triphenylphosphoranylidene)-2-butanone: a new versatile building block for substituted divinyl ketones in the synthesis of natural products
DE RISI, Carmela
2004
Abstract
Reactivity and synthetic applications of a new synthon for substituted divinyl ketones, namely 4-[(4’-methylphenyl)sulfonyl]-1-(triphenylphosphoranylidene)-2-butanone, are reviewed. The title compound has been conveniently used in “tandem” reactions allowing for the construction of six-membered hetero- and carbocyclic rings, either in homogeneous-phase or solid-phase. Moreover, generation of its alpha-sulfonyl anion offered an easy access to multifunctionalized linear carbon frameworks. The compounds obtained through the use of 4-[(4’-methylphenyl)sulfonyl]-1-(triphenylphosphoranylidene)-2-butanone represented convenient precursors for the synthesis of several natural products, such as (±)-epibatidine, (-)-anabasine, (±)-pyrenophorin and carbacephams.I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
