Crossed coupling of functionalised ketones by low valent titanium (the McMurry reaction): a new stereoselective synthesis of tamoxifen
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 475-477
- https://doi.org/10.1039/p19860000475
Abstract
Low valent titanium-mediated crossed coupling of substituted benzophenones of the type 4-XPhCOPh, where X = MeO, ClCH2CH2O, BrCH2CH2O, CF3C6H4O, HO and Me2NCH2CH2O, with propiophenone affords the corresponding but-1-enes in high yield with a marked preponderance of the Z-isomer in most cases. Remarkably, when X = OH the Z:E ratio is 9:1. The value of this method is illustrated by simple syntheses of (Z)-1-{4-[2-(N,N-dimethylamino)ethoxy]phenyl}-1,2-diphenylbut-1-ene (Tamoxifen) a drug widely used in the treatment of oestrogen-dependent breast tumours.This publication has 1 reference indexed in Scilit:
- Tamoxifen antiestrogens. A comparison of the activity, pharmacokinetics, and metabolic activation of the cis and trans isomers of tamoxifenThe Journal of Steroid Biochemistry and Molecular Biology, 1982