Synthesis of (+)- and (-)-Homononactic Acid from (S)-1,2-Epoxybutane. Total Synthesis of Tetranactin by 'Reverse Coupe du Roi'

DOI: 10.1039/c39860000996

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 996 - 998 (1986)

Update date:2022-07-31

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Authors:

Schmidt, Ulrich

Werner, Juergen

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Article abstract of DOI:10.1039/c39860000996

The synthesis of (+)- and (-)-homononactic acid was achieved in 6 steps and 4 steps respectively starting with the raction 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.

Full text of DOI:10.1039/c39860000996

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