Tributyltin, building block

Allenyl ethers are useful key building blocks for the synthesis of a-methylene-y-butyrolactones [129, 130], The synthesis of the antileukemic botryodiplodin was accomplished with the crucial steps briefly presented in Scheme 8.56. Bromoallenyl ethers 225 were easily prepared by base-induced isomerization from the corresponding /3-bromoalkyl alkynyl ether compounds and then subjected to electrophilic bro-mination with NBS. The resulting acetals 226 were converted into 2-alkoxy-3-methy-lenetetrahydrofurans 227 by dehydrohalogenation of the alkenyl bromide unit to an alkyne and subsequent radical cyclization employing tributyltin hydride [130],... 

They could be trapped with a variety of electrophiles such as aldehydes, water, carbon dioxide, trimethylsilyl chloride, tributyltin chloride to give the corresponding difluorovinyl derivatives [132-138] (Scheme 52), which were demonstrated to be versatile and useful building blocks for the synthesis of organo-fluorine compounds. 

Dinucleoside units linked by all-carbon chains have been prepared as outlined in Scheme 16, the building block 211 being obtained by oxidative cleavage of a C-allyl group, itself put in place by reaction of a radical at C-3 with allyl tributyltin. O... 

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