Asymmetric total synthesis of naturally occurring (R)-(–)-enantiomer of tylophorine via intramolecular double Michael reaction
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 2287-2292
- https://doi.org/10.1039/p19900002287
Abstract
The first asymmetric total synthesis of the naturally occurring (R)-(–)-enantiomer (1) of tylophorine was achieved with high enantioselectivity via the intramolecular double Michael reaction of α,β-unsaturated esters (10) and (20), having two different chiral auxiliaries, with t-butyldimethylsilyl trifluoromethanesulphonate in the presence of triethylamine. (–)-Phenylmenthol and (2R,4S,5R)-(–)-4-(t-butyldimethylsiloxymethyl)-5-hydroxy-2-phenyl-1,3-dioxane, readily available from D-glucose, were used as chiral auxiliaries.Keywords
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