Stereoselective synthesis of (8β, 14α)-11-methoxycarbonyl-13β-(p-bromophenyl)-17-acetylgona-1,3,5(10)-trienes

Add time:09/02/2019    Source:sciencedirect.com

Titanium tetrachloride mediated dialkylation of methyl 4-p-bromophenyl-4-oxobutanoate ethylene ketals 2 by 1,8-bis(trimethylsilyl)-2,6-octadiene 1 (BISTRO) led to a mixture of methyl dl and meso-3-(1-p-bromophenyl-2,5-divinylcyclopentan-1-yl)-propanoates 3. Iodolactonisation, reduction with Bu3SnH, Jones oxidation, methoxycarbonylation, alkylation by iodobenzocyclobutene, demethoxycarbonylation and then pyrolysis led to the title compounds.

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