Bridging of macrodithionolactones to bicyclic systems. Synthesis and modeling of oxapolycyclic frameworks

…, SA DeFrees, EA Couladouros, Y Abe…

Index: Nicolaou; Hwang; Marron; DeFrees; Couladouros; Abe; Carroll; Snyder Journal of the American Chemical Society, 1990 , vol. 112, # 8 p. 3040 - 3054

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Citation Number: 105

Abstract

Abstract: A new reaction involving bridging of macrodithionolactones to bicyclic systems is described. A series of macrodiolides was prepared and converted to the requisite macrodithionolactone. The latter substrates were induced to undergo bridging across the macrocyclic ring by exposure to sodium naphthalenide, leading to stable bicyclic systems upon addition of methyl iodide. The mixed thioketals so obtained were converted to a ...

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