Synthesis of (+)- and (–)-homononactic acid from (S)-1,2-epoxybutane. Total synthesis of tetranactin by ‘reverse coupe du roi’
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 13,p. 996-998
- https://doi.org/10.1039/c39860000996
Abstract
The synthesis of (+)- and (–)-homononactic acid was achieved in 6 steps and 4 steps respectively starting with the reaction of 2-lithium-5-vinylfuran and (S)-(–)-1,2-epoxybutane; both enantiomers were used in the construction of the achiral macrolide antibiotic tetranactin by esterification and subsequent lactonisation with the thiolester of 3-cyano-4,6-dimethyl-2-thiopyridone.Keywords
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