Formation of 9, 10-Unsaturation in the Mitomycins: Facile Fragmentation of β-Alkyl-β-aryl-α-oxo-γ-butyrolactones

FE Ziegler, MY Berlin, K Lee, AR Looker

Index: Ziegler, Frederick E.; Berlin, Michael Y.; Lee, Kyungae; Looker, Adam R. Organic Letters, 2000 , vol. 2, # 23 p. 3619 - 3621

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Citation Number: 11

Abstract

Prior to exploring the introduction of oxygen at C 9a , prudence dictated that a method be developed first for excising the atoms of the allyl ether moiety of 6 to produce a styrene. Although the exocyclic double bond of 6 could be readily isomerized to the endo cyclic position [cat. (Ph 3 P) 3 RhCl, DABCO, aqueous EtOH, 95 °C, 83%], efforts to functionalize or cleave oxidatively the endo cyclic double bond were unsuccessful. However, olefin 6 was converted to ketone 8 by ...