Selective conversion of bromo oxirane into tetrahydropyranylacrylate by epoxide ring opening
Abstract
In order to construct the tetrahydropyran ring of rhopaloic acid A and
hippospongic acid A, the ring-expansion of methyl
2-bromomethyl-6,7-epoxyhept-2-enoate with various acids was studied;
treatment of the bromo oxirane with Lewis acids (TiBr
4
,
MgBr
2
and ZnBr
2
) afforded a tetrahydrofuran
derivative as the major product, while reaction of the oxirane with silver
salt (AgNO
3
/KPF
6
) gave a tetrahydropyran derivative
as the major product.
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