An approach to the C(17)–C(24) fragment of bryostatins: applications of stereoselective trisubstituted alkene formation by palladium(0) catalysed coupling of enol acetates and vinylic bromides
- 1 January 1998
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 17,p. 2865-2872
- https://doi.org/10.1039/a803425g
Abstract
The enol acetate 26 couples stereospecifically with the vinylic bromides 25 and 29 in the presence of tributyltin methoxide and a catalytic amount of dichlorobis(tri-o-tolylphosphine)palladium to give the βγ-unsaturated ketones 27 and 30 with retention of double-bond position and geometry. The βγ-unsaturated ketone 42 which has stereochemistry and functionality corresponding to the C(17)–C(24) fragment of the C(20)-deoxybryostatins, is similarly prepared from the enol acetate 26 and the vinylic bromide 41 and can be deprotected to give the hydroxyketone 43.Keywords
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