Dialkylation of 2,3-butanedione diketal with 1,8-bis(trimethylsilyl)-2,6-octadiene (BISTRO). Application to the synthesis of estrone derivatives

Add time:08/08/2019    Source:sciencedirect.com

Titanium tetrachloride mediated-dialkylation of 2,3-butanedione ketal 2 by 1,8-bis(trimethylsilyl)-2,6-octadiene (BISTRO) 1 led to 1-acetyl-1-methyl-2,5-divinylcyclopentane 4. This latter was methoxycarbonylated (NaH/dimethylcarbonate) and then alkylated with iodobenzocyclobutene (Cs2CO3/acetone) to give a benzocyclobutenic intermediate 6, whose thermolysis provided the 12-oxo-estrane derivatives 8–11.

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