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Synthesis of the optically active hexahydrobenzofuran nucleus of the avermectins






Tetrahedron Letters 29(28): 3415-3418

Synthesis of the optically active hexahydrobenzofuran nucleus of the avermectins

A preparation of an optically pure hexahydrobenzofuranone subunit common to the milbemycin-avermectin macrocycles is reported for 1,4-anhydrosorbitol.

Accession: 001962639

DOI: 10.1016/0040-4039(88)85177-3

Download PDF Full Text: Synthesis of the optically active hexahydrobenzofuran nucleus of the avermectins



Related references

Michael T.C.immins; John G.L.ver, 1986: Synthesis of the hexahydrobenzofuran subunit of the milbemycins and the avermectins. A synthesis of the hexahydrobenzofuran subunit of milbemycins J and K has been accomplished in 17 steps from 4-methyl-1,4-pentadienol.

Ferezou J.P.; Julia M.; L.Y.; Liu L.W.; Pancrazi A., 1990: Enantioselective synthesis of the hexahydrobenzofuran part of avermectins. 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...

Lee K C.; W.J.C.C.; Yen K F.; Uang B J., 1990: Enantioselective synthesis of the hexahydrobenzofuran subunit of the avermectins and the milbemycins. Tetrahedron Letters 31(25): 3563-3566

Parsons, P., J.; Willis, P.; Eyley, S.C., 1992: A synthesis of the hexahydrobenzofuran portion of the avermectins: I. Model studies. A tandem radical cyclization has been used to construct a model for the synthesis of the hexahydrobenzofuran moiety present in the avermectins.

Barrett, A.; Capps, N., 1986: Synthetic approaches to the avermectins: studies on the hexahydrobenzofuran unit. The condensation reaction of 2-lithio-2-lithio-oxymethyl-1,3-dithiane with an epoxy-ketone is used as the key step in a novel approach to the avermectin southern hexahydrobenzofuran unit.

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