The diazo ketone approach to the isoprostanes
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- 作者：Taber ; Douglass F. ; Hoerrner ; R. Scott ; Herr ; R. Jason ; Gleave ; D. Mark ; Kanai ; Kazuo ; Pina ; Richard ; et. al.
- 关键词：Isoprostanes ; Aldol condensation ; Cyclization ; Diazo ketone ; Cyclopropane ; Mislow rearrangement ; Mitsunobu ; Rhodium catalyst ; Copper catalyst
- 刊名：Chemistry and Physics of Lipids
- 出版年：2004
- 出版时间：March, 2004
- 年：2004
- 卷：128
- 期：1-2
- 页码：57-67
- 全文大小：158 K
文摘
A general synthetic approach to the isoprostanes has been established, based on intermolecular aldol condensation of a diazo ketone with an unsaturated aldehyde, followed by cyclization of the resulting diazo ketone to the cyclopropane. Subsequent kinetic opening with thiophenol followed by further elaboration then leads to the isoprostane. The history of this approach and the details of its development are discussed.