Tetrahedron p. 6881 - 6888 (1988)
Update date:2022-07-29
Topics:
Lygo, Barry
O'connor, Norval
Wilson, Peter R.
Presented here are several examples which demonstrate that ether substituents α- or β- to an epoxide ring can be tolerated in the ring-opening reaction with β-keto ester dianions.Subsequent acid-promoted cyclisation of the γ-hydroxy β-ketoesters then leads to synthetically useful tetrahydrofurans, as demonstrated by application of this approach to the preparation of (+/-)-methyl nonactate and (+/-)-methyl 8-epi-nonactate.
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Doi:10.1016/0223-5234(88)90140-7
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