Lithiation destannylative

Verlhac and colleagues have shown the destannylative lithiation-induced [l,2]-retro-Brook rearrangement of siloxyvinyltins (equation 99) ° . This rearrangement provides the corresponding acylsilanes (equation 99). 

In view of the C-5-selectivity observed in lithiations, the selective 5-destannylation of a 4,5-di(tri- -butylstannyl)isoxazole is useful. This nice sequence utilised a coupling to a 2-iodonitrobenzene hydrogenation/hydrogenolysis caused ring cleavage of the isoxazole and produced an intermediate which cyclised with loss of water to give the indole. 

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