Lewis acid catalysed rearrangement of 7,11-epoxyisogermacrone. Formation of a new carbon skeleton

DOI: 10.1016/S0040-4020(01)86568-6

Source and publish data:

Tetrahedron p. 6399 - 6406 (1991)

Update date:2022-08-05

Topics:

Authors:

St. Enev, Valentin

Tsankova, Elena T.

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Article abstract of DOI:10.1016/S0040-4020(01)86568-6

The fluorohydrin 8 has been found to be the main product of the reaction of 7,11-epoxyisogermacrone 3 with BF₃Et₂O. When TMS-OTf is employed, 3 undergoes an unusual rearrangement leading to the product 10 with a new bicyclic carbon skeleton. The mechanism of the reaction is discussed.

Full text of DOI:10.1016/S0040-4020(01)86568-6

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