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Synlett 1990; 1990(12): 766-769
DOI: 10.1055/s-1990-21245
DOI: 10.1055/s-1990-21245
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Enantioselective Synthesis of the Hexahydrobenzofuran Part of Avermectins
Further Information
Publication History
Publication Date:
08 March 2002 (online)
An asymmetric synthesis of the southern C1 -C9 bicyclic fragment of avermectins has been developed in 13 steps from a propargyl ether and 2-methylhept-2-en-6-one via an acyclic diester intermediate [dimethyl (2R,3S)-3, 4-isopropylidenedioxy-4-methyl-2-propargyloxyheptanedioate]. A Sharpless catalytic epoxidation reaction and a stepwise Dieckmann reaction-radical cyclisation approach were used for the construction of the optically active hydrobenzofuran system.