Asymmetric total synthesis of(–)-protoemetinol,(–)-protoemetine,(–)-emetine, and (–)-tubulosine by highly stereocontrolled radical cyclisations
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 1469-1476
- https://doi.org/10.1039/p19900001469
Abstract
Both enantiomers of the menthyl half-esters (10) and (23) of ethylmalonic acid were converted into(+)-(4S,5R)-4-(2-benzyloxyethyl)-5-ethyl-3,4,5,6-tetrahydro-2-pyrone (18). A mixture of the trans-(18) and cis-lactones (19) in a ratio of ca. 4 : 1 was prepared by way of radical cyclisation of the (E)-α,β-unsaturated esters (16), while the former (18) was synthesised with high stereoselection by the cyclisation of the (Z)-esters (26). The lactone (18) was enantioselectively transformed into (–)-protoemetimol (5) and (–)-protoemetine (4), correlated to (–)-emetine (1) and (–)-tubulosine (3).This publication has 32 references indexed in Scilit:
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